Phenyl-substituted sulfonamides

ABSTRACT

Novel N-[pyrimidin-2-yl]- and [triazin-2-yl]-aminocarbonyl]-1,3-benzodioxolesulfonamides and 1,4-benzodioxansulfonamides are useful as plant growth regulants and in particular as herbicides.

CROSS REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of my copending applicationU.S. Ser. No. 649,542, filed Sept. 11, 1984, now U.S. Pat. No.4,595,407, which in turn is a divisional application of U.S. Ser. No.437,366, filed Nov. 1, 1982, now U.S. Pat. No. 4,502,882, which in turnis a continuation-in-part of my copending application U.S. Ser. No.363,379 filed Mar. 29, 1982, now abandoned.

BACKGROUND OF THE INVENTION

This invention relates to benzodioxolesulfonamides andbenzodioxansulfonamides which are useful as plant growth regulants andin particular as herbicides.

Chem. Ber., 105, 2791 (1972) describes the preparation ofN-butylcarbamoyl-p-toluenesulfamate, but does not claim utility as apesticide: ##STR1##

German Pat. No. 940,292 describes the preparation ofN-[arylcarbamoyl]arylsulfamides and claims utility as textileassistants, pharmaceuticals and pesticides: ##STR2## wherein each of Xand X¹ is H, or each is ethoxy.

Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches thepreparation of compounds of Formula (i), and their use as general orselective herbicides: ##STR3## wherein R₁ and R₂ may independently bealkyl of 1-4 carbon atoms; and

R₃ and R₄ may independently be hydrogen, chlorine or alkyl of 1-4 carbonatoms.

French Pat. No. 1,468,747 discloses the following para-substitutedphenylsulfonamides, useful as antidiabetic agents: ##STR4## wherein R=H,halogen, CF₃ or alkyl.

Logemann et al., Chem. Ab., 53, 18052g (1959), disclose a number ofsulfonamides, including uracil derivatives and those having the formula:##STR5## wherein R is butyl, phenyl or ##STR6## and R₁ is hydrogen ormethyl.

When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g),the compounds in which R is butyl and phenyl were most potent. The otherwere of low potency or inactive.

Wojciechowski, J. Acta. Polon. Pharm. 19, p. 121-5 (1962) [Chem. Ab., 591633 e] describes the synthesis ofN-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide:##STR7## Based upon similarity to a known compound, the author predictedhypolycemic activity for the foregoing compound.

Undesired vegetation can cause substantial damage to useful crops,especially agricultural products that satisfy man's basic food and fiberneeds, such as cotto, rice, corn, wheat, soybean and the like.

Although a wide variety of materials are available which can be used forkilling or inhibiting (controlling) the growth of undesired vegetationthe need exists for still more effective herbicides that destroy orcontrol weeds without causing significant damage to useful crops.

SUMMARY OF THE INVENTION

This invention relates to novel compounds of Formula I and Formula II,suitable agricultural compositions containing them, and theirmethod-of-use as general and selective pre-emergence and post-emergenceherbicides. ##STR8## wherein W is O, S, SO or SO₂ ;

W₁ is O, S, SO or SO₂ ;

R₁ is H or CH₃ ;

R₂ is H or C₁ -C₄ alkyl;

R₃, R₄, R₅, R₆ and R₇ are independently H or CH₃ ;

A is ##STR9## X is CH₃, OCH₃, or Cl; Y is C₂ H₅, CH₃, OCH₃, OC₂ H₅, CH₂OCH₃, NH₂, NHCH₃, SCH₃, N(CH₃)₂, CH(OCH₃)₂ or ##STR10## Z is CH or N; X₁is CH₃ or OCH₃ ;

G is O or CH₂ ;

X₂ is C₁ -C₃ alkyl or CH₂ CF₃ ; and

Y₂ is OCH₃, OC₂ H₅, SCH₃ or SC₂ H₅ ;

provided that when X is Cl, then Z is CH and Y is NH₂, NHCH₃, N(CH₃)₂,or OCH₃ ; and their agriculturally suitable salts.

Preferred for reasons of higher herbicidal activity and/or morefavorable ease of synthesis are:

(1) Compounds of Formula I where W and W₁ have identical values.

(2) Compounds of Formula II where W and W₁ have identical values.

(3) Compounds of Preferred 1 where A is ##STR11## and R₇ is H.

(4) Compounds of Preferred 2 where A is ##STR12## and R₇ is H. (5)Compounds of Preferred 3 where R₂ is H or CH₃.

(6) Compounds of Preferred 5 where Y is CH₃ or OCH₃.

(7) Compounds of Preferred 6 where W and W₁ are O or S.

(8) Compounds of Preferred 6 where W and W₁ are SO or SO₂.

Specifically Preferred are:

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide;

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide;

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide;

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide;

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide;and

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide.

DETAILED DESCRIPTION OF THE INVENTION Synthesis

The compounds of Formulae (I) and (II) can be prepared by one of themethods described below in Equations 1 and 2.

As shown in Equation 1, compounds of Formula I can be prepared byreaction of the sulfonamide of Formula (III) with an appropriate methylheterocyclic carbamate of Formula (IV) in the presence of an equimolaramount of trimethylaluminum, wherein R₁, R₂, R₇, W₁, W and A are aspreviously defined. ##STR13##

The reaction of Equation 1 takes place in methylene chloride at refluxor ambient temperature for 16-96 hours under an inert atmosphere. Theproduct can be isolated after the sequential addition of aqueous aceticacid and hydrochloric acid to the reaction mixture followed by thepartitioning of the product into methylene chloride. The product can bepurified via crystallization from such solvents as n-butyl chloride,diethyl ether, tetrahydrofuran, or methylene chloride or by silicamedium pressure liquid chromatography.

As shown in Equation 2, compounds of Formula (II) can be prepared byreaction of the sulfonamide of Formula (V) with an appropriate methylheterocyclic carbamate of Formula (IV) in the presence of an equimolaramount of trimethylaluminum, wherein R₃ to R₇, W₁, W and A are aspreviously defined. ##STR14##

The reaction of Equation 2 is performed in methylene chloride at refluxfor 16-72 hours under an inert atmosphere. The product is isolated uponsequential addition of aqueous acetic acid and hydrochloric acid to thereaction mixture followed by the partitioning of the product intomethylene chloride. The product is purified via crystallization fromsolvents such as n-butyl chloride, diethyl ether or methylene chlorideor by silica medium pressure liquid chromatography.

As shown in Equation 3, the sulfonamides of Formula (III) wherein R₁ andR₂ are not H and W₁ and W are as previously defined can be prepared fromthe appropriate 1,3-benzodioxole of Formula (VI) via the lithiumsulfinate of Formula (VII). ##STR15##

Reaction of the arene of Formula (VI) with a butyllithium in ether ortetrahydrofuran in the presence or absence of a chelating agent such asN,N,N',N'-tetramethylethylene diamine at -78° to ambient temperature for2-16 hours followed by contacting with sulfur dioxide at -78° to ambienttemperature until no further exotherm is noted results in the formationof the lithium sulfinate of Formula (VII). The 4-sulfonamide of Formula(III) is isolated in a two-step sequence upon reaction of the lithiumsulfinate of Formula (VII) with N-chlorosuccinimide in glacial aceticacid at 15° to 25° C. followed by contacting the product with an aqueoussolution to give the sulfonyl chloride. The sulfonyl chloride is thencontacted with excess ammonia in diethyl ether or methylene chloride at10°-20° C. The 1,3-benzodioxoles of Formula (VI) wherein W₁ and W are Ocan be prepared according to the procedures of C. M. Yoder and J. J.Zuckerman, J. Heterocycl. Chem., 1967, 4, 166; E. R. Cole et al., Aust.J. Chem., 1980, 33, 675; and W. Bonthrone and J. W. Cornforth, J. Chem.Soc. (C), 1969, 1202.

The 1,3-benzodithioles and the benzoxathioles of Formula VI, wherein W₁and W are O or S, can be prepared according to the procedures suggestedby S. Cabiddu et al. Synthesis, 1976, 797; G. Scherowsky and J. Weiland,Chem. Ber. 1974, 3155; and A. Pelter et al. Tetrahed. Lett. 1978, 26,2345. Compounds of Formula (VI) wherein W₁ and/or W are higher oxidationstates of sulfur can be prepared from compounds of Formula (VI), whereinW₁ and W are not both O, or SO₂ or a combination of O and SO₂, upontreatment with the appropriate equivalents of 30% hydrogen peroxide inacetic acid at ambient temperature or reflux for 4-17 hours as suggestedby W. Parham et al. J. Am. Chem. Soc., 1953, 75, 1953; permanganatetreatment according to the procedure of D. Greenwood and H. Stevenson,J. Chem. Soc., 1953, 1514, or via periodate oxidation. Mixtures ofoxidized benzodithioles and benzoxathioles, obtained by theseprocedures, can be purified via fractional crystallization or columnchromatography.

An alternative route to the preparation of the 4-sulfonamide of Formula(III), wherein W₁ and W are O or S and R₁ and R₂ are as previouslydefined, including H, from bromobenzene of Formula (VIII) is illustratedbelow in Equation 4. ##STR16##

The 3-bromocatechol of Formula (VIII) can be prepared according to theprocedure of H. S. Mason, J. Am. Chem. Soc. 1947, 69, 2241. The4-bromo-1,3-benzodioxole of Formula (IX) can be prepared from3-bromocatechol of Formula (VIII) via procedures similar to thosedescribed by W. Bonthrone and J. W. Cornforth, J. Chem. Soc. (C), 1969,1202. The bromo thiocatechols and bromothiophenols of Formula (VIII) canbe prepared according to the procedures of L. Horner et al., Phosphorusand Sulfur, 1982, 2, 353 and A. Ferretti, Org. Synth., 1973, Coll Vol V,419. The 4-bromo-1,3-benzodithioles and the bromoxathioles of Formula(IX) can be prepared according to the procedure of S. Cabiddu et al.,Synthesis, loc. cit. A metal-halogen interchange of the bromo compoundof Formula (IX) in an ether solution at -70° to -78° C. using 1.1equivalents of n-butyllithium followed by sulfur dioxide contact at -45°to -78° C. can afford the lithium sulfinate of Formula (VII). Thesulfonamide of Formula (III), can be prepared from the sulfinate ofFormula (VII) by the N-chlorosuccinimide, ammonia procedures shown inEquation 3.

An alternative route to the preparation of 4-sulfonamides of Formula(III) wherein W₁ and W can be higher oxidation states of sulfur isillustrated in Equation 5. ##STR17##

Reaction of the 4-sulfonamides of Formula (IIIa) wherein W₁ and W arenot both O or SO₂ or a combination of O and SO₂ and R₁ and R₂ are aspreviously defined, with 30% hydrogen peroxide as suggested by W. Parhamet al., J. Am. Chem. Soc., loc. cit.; permangonate reaction according tothe procedure of D. Greenwood and H. Stevenson, J. Chem. Soc., loc.cit.; or periodate reaction may afford the 4-sulfonamides of Formula(IIIb) wherein W₁ ' and W' may be higher oxidation states of sulfur.Mixtures of oxidized sulfonamides, obtained by these procedures, can bepurified via fractional crystallization or column chromatography.

As illustrated below in Equation 6, 5-sulfonamides of Formula (V),wherein R₃ through R₆ are not H and W₁ and W are as previously definedcan be prepared from arenes of Formula (X) via the lithium sulfinate ofFormula (XI) according to the procedures of Equation 3. ##STR18##

The 1,4-benzodioxans of Formula (X) wherein W₁ and W are O can beprepared according to the procedures of Schroth et al., Z. Chem., 1967,7, 152 and B. N. Ghosh, J. Chem. Soc., 1915, 107, 1591, W. Adam et al.,Synthesis, 1982, 322, A. Bashall and J. Collins, Tetrahed. Lett., 1975,40, 3489.

The 1,4-benzodithians and the benzoxathians of Formula (X), wherein W₁and W are both S or a combination of S and O can be prepared accordingto the procedures of W. Parham et al., J. Am. Chem. Soc., loc. cit. andS. Cabiddu et al., Synthesis, loc. cit. Compounds of Formula (X) whereinW₁ and/or W can include higher oxidation states of sulfur can beprepared upon hydrogen peroxide, permanganate or periodate treatment assuggested by W. Parham et al., J. Am. Chem. Soc., loc. cit. and D.Greenwood and H. Stevenson, J. Chem. Soc., loc. cit. Mixtures ofoxidized benzodithians and benzoxathians, obtained by these procedures,can be purified via fractional crystallization or column chromatography.

An alternative route to the preparation of the 5-sulfonamides of Formula(V), wherein W₁ and W are O or S and R₃ through R₆ are as previouslydefined and include H from the bromobenzenes of Formula (VIII) via thecyclic arene of Formula (XII) and lithium sulfonate of Formula (XI)according to the procedures of Equation 4 is illustrated in Equation 7.##STR19##

The preparation of the bromobenzenes is illustrated in the discussion ofEquation 4. The bromobenzodioxans of Formula (XII) can be preparedaccording to the procedures of Schroth et al., Z. Chem., loc. cit. andB. Ghosh, J. Chem. Soc., loc. cit. The bromobenzodithians andbromobenzoxathians of Formula (XII) can be prepared according to theprocedures of the benzodithians and benzoxathians of Formula (X),discussed in Equation 6.

As illustrated in Equation 8, the 5-sulfonamides of Formula (Vb) whereinR₃ through R₆ are as previously defined and W₁ and W may include higheroxidation states of sulfur, may be prepared via the 5-sulfonamides ofFormula (Va), wherein W₁ and W are not both O or SO₂ or a combination ofO and SO₂ and R₃ through R₆ are as previously defined, according to theprocedures of Equation 5. ##STR20##

Equation 9 illustrates the preparation of the requisite methylheterocyclic carbamates of Formula (IV) utilized in Equations 1 and 2,wherein R₇ and A are as previously defined. ##STR21##

According to Equation 9, a heterocyclic amine of Formula (XIII) iscontacted with two equivalents of sodium hydride and excessdimethylcarbonate to form (IV). This reaction is performed in an inertsolvent such as tetrahydrofuran at 25° to 70° C. for 1 to 24 hours. Theproduct is isolated by (a) addition of two equivalents of concentratedhydrochloric acid and aqueous saturated sodium chloride and (b)separation of the organic phase followed by concentration to dryness invacuo.

The synthesis of the pyrimidine and triazine amines of Formula (XIII)has been reviewed in "The Chemistry of Heterocyclic Compounds," a seriespublished by Interscience Publ., New York and London. The2-aminopyrimidines are described by D. J. Brown in "The Pyrimidines,"Vol. XXVI of this series. The 2-amino-1,3,5-triazines can be preparedaccording to methods described by E. M Smolin and L. Rapaport in"s-Triazines and Derivatives," Vol. XIII of the same series. Thesynthesis of triazines is also described by F. C. Schaefer, U.S. Pat.No. 3,154,547 and by K. R. Huffman and F. C. Schaefer, J. Org. Chem.,1963, 28, 1816.

Braker, Sheehan, Spitzmiller and Lott, J. Am. Chem. Soc., 69, 3072(1947) describe the preparation of6,7-dihydro-4-methoxy-5H-cyclopentapyrimidin-2-amine by the followingsequence of reactions. ##STR22##

An analogous sequence of reactions can be used to prepare5,6,7,8-tetrahydro-4-methoxy-2-quinazolinamine. ##STR23##

Mitter and Bhattacharya, Quart. J. Indian Chem. Soc., 4, 152 (1927)describe the preparation of5,6,7,8-tetrahydro-4-methyl-2-quinazolinamine as follows: ##STR24##

Similarly, 6,7-dihydro-4-methyl-5H-cyclopentapyrimidin-2-amine can beprepared by the condensation of 2-acetylcyclopentanone with guanidinecarbonate, but preferably under acidic conditions, removing the waterformed. ##STR25##

Shrage and Hitchings, J. Org. Chem., 16, 1153 (1951) describe thepreparation of 5,6-dihydro-4-methylfuro[2,3-d]pyrimidin-2-amine by thefollowing sequence of reactions ##STR26##

An analogous sequence of reactions can be used to prepare6,7-dihydro-4-methyl-5H-pyrano[2,3-d]pyrimidin-2-amine starting with2-acetyl-8 valerolactone [Korte and Wusten, Tetrahedron 19, 1423(1963)]. ##STR27##

5,6-Dihydro-4-methoxyfuro[2,3-d]pyrimidin-2-amine can be prepared by themethod of Braker et al., J. Am. Chem. Soc., 69, 3072 (1947), using5,6-dihydro-4-hydroxyfuro[2,3-d]pyrimidin-2-amine [Svab, Budesinski andVavrina, Collection Czech. Chem. Commun., 32, 1582 (1967)]. ##STR28##

An analogous sequence of reactons can be used to prepare6,7-dihydro-4-methoxy-5H-pyrano[2,3-d]pyrimidin-2-amine. ##STR29##

Caldwell, Kornfeld and Donnell, J. Am. Chem. Soc., 63, 2188 (1941),describe the preparation of 6,7-dihydro-5H-cyclopentapyrimidin-2-amineby the following sequence of reactions. ##STR30##

Fissekis, Mules and Brown, J. Org. Chem., 29, 2670 (1964), describe thepreparation of 2-amino-4-hydroxy-5-(2-hydroxyethyl)pyrimidine which canbe converted to 5,6-dihydrofuro[2,3-d]pyrimidin-2-amine by dehydration.##STR31##

Preparations of 3-amino-1,2,4-triazoles are known in the art and1,2,4-triazoles are reviewed in The Chemistry of Heterocyclic Compounds"Triazoles 1,2,4" (John Wiley and Sons, New York, 1981). Commonly usedstarting materials containing nitrogen are N-aminoguanidine, hydrazine,alkylhydrazines, cyanamide, ethyl cyanoacetaimidate, dimethylcyanodithioimidocarbonate, dimethyl cyanoimidocarbonate,ethoxymethylenecyanamide, and acylhydrazines. Some literature synthesesare illustrated below. Using these techniques or suitable modificationsthat would be apparent to one skilled in the art, the3-amino-1,2,4-triazole intermediates can be readily prepared.

Heating equimolar amounts of ethyl propionimidate hydrochloride andN-aminoguanidine nitrate in pyridine gives 3-amino-5-ethyltriazole;German Pat. No. 1,073,499 (1960); Berichte, 96, 1064 (1963). ##STR32##Condensation of hydrazine with ethyl N-cyanoacetimidate yields3-amino-5-methyltriazole; Journal of Organic Chemistry, 28, 1816 (1963).##STR33## Trifluoromethyl-3-aminotriazole can be obtained by thermaldehydration of the hydrazide of trifluoroacetic acid. Zh. Obshch. Khim.,39, 2525 (1969); Chemical Abstracts, 72: 78954v (1970). ##STR34## U.S.Pat. No. 2,835,581 (1958) teaches the preparation of3-amino-5-(hydroxymethyl)triazole from N-aminoguanidine and glycolicacid and British Pat. No. 736,568 (1955) describes the synthesis of3-amino-5-mercaptotriazole. ##STR35## Condensing hydrazine with dimethylcyanodithioimidocarbonate in acetonitrile gives3-amino-5-methylthio-1,2,4-triazole while reaction of hydrazine withdimethyl N-cyanoimidocarbonate produces3-amino-5-methoxy-1,2,4-triazole; Journal of Organic Chemistry, 39, 1522(1974). ##STR36##

Reaction of substituted hydrazines with N-cyanothioimidocarbonates(prepared according to the procedure given in D. M. Wieland, Ph.D.Thesis, 1971, pp. 123-124) yields disubstituted aminotriazoles as shownbelow. ##STR37## wherein X₃ is C₁ -C₃ alkyl; and

Y₃ is C₁ -C₂ alkoxy.

Furo[2,3-d]pyrimidine Intermediates

The pyrimidine intermediates XIV in which Z is hydrogen or methyl and Xis methyl have been reported in the literature by E. Bisagni et al.,[Bul. Soc. Chim. Fr., 803 (1969)]. Apparently more efficient procedureis depicted in Equation 10 for the case in which Z is hydrogen.##STR38##

The keto-ester precursors XV are prepared by well known literaturemethods, e.g., J. F. Tinker and T. E. Whatmough, J. Amer. Chem. Soc.,74, 5235 (1952).

Treatment of XIV with an excess of guanidine carbonate in an organicsolvent, preferably a polar aprotic solvent such as dimethylsulfoxide(DMSO), dimethylformamide (DMF), or N,N-dimethylacetamide, at atemperature of 80° to 200°, preferably 100° to 160°, ambient pressureand preferably under an inert atmosphere, yields both XIVa and XVI asproducts. The products are isolated upon dilution of the reactionmixture with, for example, acetone and water successively. Higherreaction temperatures and longer reaction times (e.g., in DMSO at130°-150° for 2 to 8 hours) favor the production of the furopyrimidineXIV over the uncyclized pyrimidine XVI.

Agriculturally suitable salts of compounds of Formulae (I) and (II) arealso useful herbicides and can be prepared in a number of ways known tothe art. For example, metal salts can be made by contacting compounds ofFormulae (I) and (II) with a solution of an alkali or alkaline earthmetal salt having a sufficiently basic anion (e.g. hydroxide, alkoxide,carbonate or hydroxide). Quaternary amine salts can be made by similartechniques.

Salts of compounds of Formula (I) or (II) can also be prepared byexchange of one cation to another. Cationic exchange can be effected bydirect treatment of an aqueous solution of a salt of a compound ofFormula (I) or (II) (e.g., alkali metal or quaternary amine salt) with asolution containing the cation to be exchanged. This method is mosteffective when the desired salt containing the exchanged cation isinsoluble in water, e.g., a copper salt, and can be separated byfiltration.

Exchange may also be efffected by passing an aqueous solution of a saltof a compound of Formula (I) or (II) (e.g., an alkali metal orquaternary amine salt) through a column packed with a cation exchangeresin containing the cation to be exchanged. In this method, the cationof the resin is exchanged for that of the original salt and the desiredproduct is eluted from the column. This method is particularly usefulwhen the desired salt is water-soluble, e.g., a potassium, sodium orcalcium salt.

Acid addition salts, useful in this invention, can be obtained byreacting a compound of formula (I) or (II) with a suitable acid, e.g.,p-toluenesulfonic acid, trichloroacetic acid or the like.

The compounds of this invention and their preparation are furtherillustrated by the following examples wherein temperatures are given indegrees centrigrade and all parts are by weight unless otherwiseindicated.

EXAMPLE 1 2,2-Dimethyl-1,3-benzodioxole-4-sulfonamide

To a solution of 25 g 2,2-dimethyl-1,3-benzodioxole [prepared accordingto the procedure of C. M. Yoder and J. J. Zuckerman, J. Heterocycl.Chem., 1967, 4, 166] in 300 ml ether and 200 ml tetrahydrofuran atambient temperature under nitrogen was added dropwise, 105 mln-butyllithium (1.6N in hexane). The temperature was maintained at ≈25°C. with ice bath cooling during the addition. The reaction mixture wasstirred 16 hours at room temperature. Excess sulfur dioxide was bubbledthrough the reaction mixture, kept at ≈25° C. with cooling, until nofurther exotherm was noted. The reaction mixture was stirred at roomtemperature for 18 hours followed by the addition of 10 ml isopropylalcohol. The reaction mixture was concentrated and crystallized fromether/tetrahydrofuran to give 20.5 g tan solid. The solid was added to150 ml acetic acid and the resultant mixture was cooled to 20° C. Aslurry of 12.4 g N-chlorosuccinimide in 75 ml acetic acid was addedportionwise with cooling to maintain the reaction mixture between 20°and 25° C. The reaction mixture was stirred for three hours at ambienttemperature and the solvent was removed under reduced pressure to givean oil. The oil was dissolved in methylene chloride and washed withwater. The aqueous phase was washed with methylene chloride. The organicphases were combined, dried and the solvent removed under reducedpressure to give an oil which was dissolved in 250 ml ether and cooledto 10° C. Excess ammonia (anhy.) was bubbled through the reactionmixture using ice bath cooling. The reaction mixture was warmed toambient temperature, stirred for 1 hour, and 150 ml ether was added. Thereaction mixture was washed with water, dried and concentrated underreduced pressure to give 8.1 g tan oily solid, m.p. 100°-112° C. IR (NH)3240 (NH), 3420 (NH) cm⁻¹.

¹ HNMR (DMSO-d₆): 1.7 (s, 6H); and 6.5-7.4 (m, 5H).

EXAMPLE 2 1,3-Benzodioxole-4-sulfonamide

To a solution of 18.8 g 3-bromocatechol (prepared according to theprocedure of H. S. Mason, J. Am. Chem. Soc., 1947, 69, 2241) and 10 gmethylene chloride in 150 ml dimethyl sulfoxide at ambient temperatureunder nitrogen is added 8.3 g of sodium hydroxide (powdered). Thereaction mixture is heated at 120° C. for 2 hours. Steam distillationgives 13.5 g of the solid, 4-bromo-1,3-benzodioxole. The solid isdissolved in 200 ml of tetrahydrofuran under a nitrogen atmosphere,cooled to -78° C. and treated sequentially with 42.2 ml n-butyllithium(1.6N in hexane) for 16 hours and excess sulfur dioxide until no furtherexotherm is noted. The reaction mixture is contacted with 10 mlisopropyl alcohol, concentrated in vacuo and crystallized fromether/tetrahydrofuran to give a solid. The solid is added to 150 ml ofacetic acid and cooled to 20° C. A slurry of 12 g N-chlorosuccinimide in75 ml acetic acid is added portionwise with cooling to maintain areaction temperature of 20°-25° C. The reaction mixture is stirred forthree hours at room temperature and the solvent is removed under reducedpressure to give an oil which is dissolved in methylene chloride andwashed with water. The organic phase is dried, and the solvent removedunder reduced pressure to give an oil which is dissolved in 250 ml etherand cooled to 10° C. Excess ammonia (anhy.) is bubbled through thereaction mixture with external cooling. The reaction mixture is washedwith water, dried, and concentrated under reduced pressure to give asolid.

EXAMPLE 3 Methyl (4,6-dimethoxypyrimidin-2-yl)carbamate

2-Amino-4,6-dimethoxypyrimidine (56 g) was added portionwise to 50%sodium hydride (42.8 g) in 1000 ml of dry tetrahydrofuran. Afterstirring for 0.5 hour, dimethylcarbonate (58.5 g) was added dropwisewith cooling. The mixture was stirred under nitrogen for about 16 hoursat ambient temperature. Concentrated HCl (80 ml) was added slowly asexternal cooling was used to maintain a pot temperature of about 25° C.Saturated aqueous sodium chloride (80 ml) was then added. The solventswere decanted from the precipitated solids and dried over sodiumsulfate. Filtration and evaporation of the solvents afforded the crudematerial which was recrystallized from hexane to yield 54 g of the titlecompound, m.p. 81°-83° C. The IR spectrum showed characteristicabsorption bands at 3400 and 1760 cm⁻¹.

EXAMPLE 4N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide

To a solution of 0.55 g 2,2-dimethyl-1,3-benzodioxole-4-sulfonamide,prepared in Example 1, in 30 ml methylene chloride at ambienttemperature under nitrogen was added 1.2 ml of trimethylaluminum (2M intoluene). After stirring 15 minutes at ambient temperature, 0.47 g ofmethyl [4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared accordingto the procedure of Example 3, was added and the reaction mixture washeated at reflux 16 hours. The reaction mixture was cooled to ambienttemperature and 75 ml H₂ O, 10 ml glacial acetic acid, and 10 dropshydrochloric acid were sequentially added. The organic phase wasseparated, dried, and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from a mixture of butyl chloride,hexane and ether gave 0.25 g white solid, m.p. 180°-183° C. The infraredspectrum showed a carbonyl absorption at 1705 cm⁻¹ indicative of thetitle compound.

¹ HNMR (CDCl₃): δ 1.6 (s, 6H); 2.5 (s, 3H); 4.0 (s, 3H); 6.3 (s, 1H);and 6.9-7.6 (m, 3H).

EXAMPLE 5 Methyl (4,6-dimethoxy-1,3,5-triazin-2-yl)carbamate

2-Amino-4,6-dimethoxy-1,3,5-triazine (55.3 g) was added portionwise to50% sodium hydride (38.0 g) in 1000 ml dry tetrahydrofuran at ambienttemperature under nitrogen. After the reaction mixture was stirred for1.25 hours, dimethylcarbonate (50.0 g) was added dropwise. The reactionmixture was stirred 16 hours at ambient temperature under nitrogen andconcentrated hydrochloric acid (68 ml) was slowly added followed by 100ml tetrahydrofuran. Insoluble material was removed via filtration anddiscarded. The filtrate was dried and the solvent removed under reducedpressure to give a solid which upon crystallization from ethanolafforded 43.9 g of the tital compound, m.p. 118°-122° C.

EXAMPLE 6N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide

To a solution of 1.0 g 2,2-dimethyl-1,3-benzodioxole-4-sulfonamide,prepared in Example 1, in 50 ml methylene chloride at room temperatureunder nitrogen was added 2.5 ml trimethylaluminum (2M in toluene). Afterstirring 15 minutes at room temperature, 0.7 g of methyl[4-methoxy-6-methyl-1,3,5-triazin-2-yl]carbamate, prepared according tothe procedure of Example 5, was added and the reaction mixture washeated at reflux 72 hours. The reaction mixture was cooled to roomtemperature and 75 ml ice, 3 ml glacial acetic acid, and 10 drops ofhydrochloric acid were sequentially added. The organic phase wasseparated, dried and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from a mixture of ether, methylenechloride, and hexane gave 0.1 g white solid, m.p. 160°-168° C. Theinfrared spectrum showed a carbonyl absorption at 1705 cm⁻¹ indicativeof the title compound.

¹ HNMR ((CD₃)₂ CO): δ 1.6 (s, 6H); 2.5 (s, 3H); 4.0 (s, 3H); and 6.9-7.6(m, 3H).

EXAMPLE 7 2,2-Dimethyl-1,3-Benzodithiole-4-Sulfonamide

To a solution of 69 ml s-butyllithium and 15 mlN,N,N',N'-tetramethylethylenediamine in 200 ml THF stirring at -78° C.under nitrogen was added a THF solution of 18.2 g2,2-dimethyl-1,3-benzodithiole [prepared according to the procedure ofPelter et al., Tetrahedron Lett., 1977, 225]. The temperature wasmaintained at -78° C. to -65° C. with external dry ice bath coolingduring the addition. The reaction mixture was stirred 1 hour at -78° C.Excess sulfur dioxide was bubbled through the reaction mixture, kept at-70° C. to -60° C. with cooling until no further exotherm was noted. Thereaction mixture was warmed to ambient temperature, stirred for 18 hoursand 10 ml isopropyl alcohol was added. The reaction mixture wasconcentrated and crystallized from ether/methylene chloride to give asolid. The solid is added to 150 ml of acetic acid and cooled to 20° C.A slurry of 12 g N-chlorosuccinimide in 75 ml acetic acid is addedportionwise with cooling to maintain a reaction temperature of 20°-25°C. The reaction mixture is stirred for 2 hours at room temperature andthe solvent is removed under reduced pressure to give an oil which isdissolved in methylene chloride and washed with water. The organic phaseis dried and the solvent removed under reduced pressure to give an oilwhich is dissolved in 250 ml ether and cooled to 10° C. Excess ammonia(anhy.) is bubbled through the reaction mixture with external cooling.The reaction mixture is warmed to room temperature, washed with water,dried, and concentrated under reduced pressure to give a tan solid.

EXAMPLE 8 1,3-Benzodithiole-4-sulfonamide

To a solution of 1.7 g dibromomethane and Aliquat 336® in 75 ml toluenewas added dropwise a solution of 2.2 g 3-bromothiocatechol (preparedaccording to the procedures of L. Horner et al., Phosphorus and Sulfur,1982, 2, 353 and A. Ferretti, Org. Synth., 1973, Coll. Vol. V, 419), 2.4g of 50% sodium hydroxide, and 25 ml water. The reaction mixture washeated at reflux 1.5 hour, cooled to ambient temperature and stirred 16hours. The organic phase was separated, washed with 1N sodium hydroxideand water, dried and concentrated under reduced pressure to give an oil.The oil was purified via distillation to give 1.4 g4-bromo-1,3-benzodithiole. The oil was dissolved in 60 ml oftetrahydrofuran under a nitrogen atmosphere, cooled to -70° C. andtreated sequentially with 4.5 ml n-butyllithium (1.6N in hexanes) for0.5 hour at -70° C. and excess sulfur dioxide until no further exothermwas noted. The reaction mixture was contacted with 3 ml isopropylalcohol, concentrated in vacuo and crystallized fromether/tetrahydrofuran to give a solid. The solid was added to 40 mlacetic acid and cooled to 20° C. A slurry of 0.8 g N-chlorosuccinimidein 20 ml acetic acid was added portionwise with cooling to maintain areaction temperature of 20°-25° C. The reaction mixture was stirred forthree hours at room temperature and the solvent was removed underreduced pressure to give an oil which was dissolved in methylenechloride and washed with water. The organic phase was dried, and thesolvent removed under reduced pressure to give an oil which wasdissolved in 250 ml ether and cooled to 10° C. Excess ammonia (anhy.)was bubbled through the reaction mixture with external cooling. Thereaction mixture was washed with water, dried, and concentrated underreduced pressure to give a solid.

EXAMPLE 9 2,2-Dimethyl-1,3-benzodithiole-4-sulfonamide,1,1,3,3-tetraoxide

To a solution of 10.0 g 2,2-dimethyl-1,3-benzodithiole, prepared inExample 7, in 150 ml glacial acetic acid was added dropwise withexternal cooling 34.5 ml 30% hydrogen peroxide. The reaction mixture wasstirred at room temperature one hour, heated at reflux 1 hour, cooled toambient temperature and stirred 16 hours. Aqueous sodium bisulfite andether were added to the reaction mixture and the resultant mixturewashed with sodium bisulfite, solid sodium chloride, dried andconcentrated under reduced pressure to give 7.0 g white solid, m.p.146°-148° C. The solid was dissolved in 40 ml THF at -70° C. undernitrogen and 22 ml of butyllithium (1.6N in hexanes) was added dropwisewith external cooling to maintain a maximum temperature of -65° C. Thereaction mixture was stirred 1 hour at -70° C. Excess sulfur dioxide wasbubbled through the reaction mixture, kept at -70° C. with cooling untilno further exotherm was noted. The reaction mixture was warmed toambient temperature, stirred at -70° C. for 18 hours and 10 ml isopropylalcohol was added. The reaction mixture was concentrated andcrystallized from ether/methylene chloride to give a solid. The solidwas added to 150 ml of acetic acid and cooled to 20° C. A slurry of 3.7g N-chlorosuccinimide in 75 ml acetic acid was added portionwise withcooling to maintain a reaction temperature of 20°-25° C. The reactionmixture was stirred for 2 hours at room temperature and the solvent wasremoved under reduced pressure to give an oil which is dissolved inmethylene chloride and washed with water. The organic phase was driedand the solvent removed under reduced pressure to give an oil which isdissolved in 250 ml ether and cooled to 10° C. Excess ammonia (anhy.)was bubbled through the reaction mixture with external cooling. Thereaction mixture was warmed to room temperature, washed with water,dried, and concentrated under reduced pressure to give a solid, m.p.215°-220° C.

EXAMPLE 10N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl)]-2,2-dimethyl-1,3-benzodithiole-4-sulfonamide

To a solution of 2.61 g 2,2-dimethyl-1,3-benzodithiole-4-sulfonamide,prepared in Example 7, in 45 ml methylene chloride at ambienttemperature under nitrogen was added 5 ml of trimethylaluminum (2M intoluene). After stirring 15 minutes at ambient temperature, 2.0 g ofmethyl (4-methoxy-6-methylpyrimidin-2-yl)carbamate, prepared accordingto the procedure of Example 3, was added and the reaction mixture washeated at reflux 16 hours. The reaction mixture was cooled to ambienttemperature and 75 ml H₂ O, 10 ml glacial acetic acid, and 10 dropshydrochloric acid were sequentially added. The organic phase wasseparated, dried, and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from an ether solvent gave a solid.

EXAMPLE 11N-[(4-Methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodithiole-4-sulfonamide

To a solution of 2.6 g 2,2-dimethyl-1,3-benzodithiole-4-sulfonamideprepared in Example 7, in 60 ml methylene chloride at room temperatureunder nitrogen is added 5.5 ml trimethylaluminum (2M in toluene). Afterstirring 15 minutes at room temperature, 2.0 g of methyl[4-methoxy-6-methyl-1,3,5-triazin-2-yl]carbamate, prepared according tothe procedure of Example 5, was added and the reaction mixture washeated at reflux for 72 hours. The reaction mixture was cooled to roomtemperature and 75 ml ice, 3 ml glacial acetic acid, and 10 drops ofhydrochloric acid were sequentially added. The organic phase wasseparated, dried and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from an appropriate solvent gave asolid.

EXAMPLE 12N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodithiole-4-sulfonamide1,1,3,3-tetraoxide

To a solution of 3.25 g 2,2-dimethyl-1,3-benzodithiole-4-sulfonamide,1,1,3,3-tetraoxide, prepared in Example 1, in 50 ml methylene chlorideat ambient temperature under nitrogen was added 5.5 ml trimethylaluminum(2M in toluene). After stirring 15 minutes at ambient temperature, 2.0 gof methyl 4-methoxy-6-methylpyrimidin-2-yl)carbamate, prepared accordingto the procedure of Example 3, was added and the reaction mixture washeated at reflux for 72 hours. The reaction mixture was cooled toambient temperature and 75 ml water, 10 ml glacial acetic acid, and 10drops hydrochloric acid were sequentially added. The organic phase wasseparated, dried, and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from n-butyl chloride/ether gave asolid, m.p. 191°-200° C.

IR(mull): 1690 (c=o) cm⁻¹.

NMR ((CD₃)₂ CO): δ 1.6 (s, 3H); 2.1 (s, 6H); 4.0 (s, 3H); 6.5 (s, 1H);and 8.1-9.0 (m, 3H).

EXAMPLE 13 1,3-Benzoxathiole-4-sulfonamide

To a solution of 17 g dibromomethane and Aliquat 336® in 200 ml tolueneis added dropwise a solution of 21 g 3-bromo-2-mercapto phenol [preparedaccording to the procedure of S. Cabiddu et al., Synthesis, loc. cit.]and A. Bashall and J. Collins, Tetrahed. Lett., loc. cit.] 24 g of 50%sodium hydroxide and 50 ml H₂ O. The reaction mixture is then heated atreflux for 16 hours and cooled to ambient temperature. The organic phaseis separated, washed with 1N sodium hydroxide and water, dried andconcentrated under reduced pressure to give an oil. The oil is purifiedvia distillation to give 14 g 4-bromo-1,3-benzoxathiole. The oil isdissolved in 60 ml of tetrahydrofuran under a nitrogen atmosphere,cooled to -70° C. and treated sequentially with 45 ml n-butyllithium(1.6N in hexanes) for 1 hour and excess sulfur dioxide until no furtherexotherm is noted. The reaction mixture is contacted with 2 ml isopropylalcohol, concentrated in vacuo and crystallized fromether/tetrahydrofuran to give a solid. The solid is added to 150 mlacetic acid and cooled to 20° C. A slurry of 8.0 g N-chlorosuccinimidein 30 ml acetic acid is added portionwise with cooling to maintain areaction temperature of 20°-25° C. The reaction mixture is stirred forthree hours at room temperature and the solvent is removed under reducedpressure to give an oil which is dissolved in methylene chloride andwashed with water. The organic phase is dried, and the solvent removedunder reduced pressure to give an oil which is dissolved in 250 ml etherand cooled to 10° C. Excess ammonia (anhy.) is bubbled through thereaction mixture with external cooling. The reaction mixture is washedwith water, dried, and concentrated under reduced pressure to give asolid.

EXAMPLE 14N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,3-benzoxathiole-4-sulfonamide

To a solution of 2.2 g 1,3-benzoxathiole-4-sulfonamide, prepared inExample 13, in 50 ml methylene chloride at ambient temperature undernitrogen is added 5.5 ml trimethylaluminum (2M in toluene). Afterstirring 15 minutes at ambient temperature, 2.0 g ofmethyl[4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared according tothe procedure of Example 3, is added and the reaction mixture is heatedat reflux for 16 hours. The reaction mixture is cooled to ambienttemperature and 75 ml water, 10 ml glacial acetic acid, and 10 dropshydrochloric acid are sequentially added. The organic phase isseparated, dried, and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from n-butyl chloride/ether gives asolid.

The compounds of Table I can be prepared according to the procedures ofExamples 4, 6, 10, 11, 12 and 14 using the appropriate 4-sulfonamide andcarbamate.

EXAMPLE 15 1,4-Benzodioxan-5-sulfonamide

To a solution of 43.6 g 5-bromo-1,4-benzodioxan (prepared according tothe procedures of S. Cabiddu et al., Synthesis, loc. cit.) and in 400 mltetrahydrofuran -70° under nitrogen was added dropwise 127 ml ofn-butyllithium (1.6N in hexane). The temperature was maintained at -70°C. with dry ice/acetone cooling during the addition. The reactionmixture was stirred 0.5 hour at -70° C. Excess sulfur dioxide wasbubbled through the reaction mixture, kept at -60° to -70° C. withcooling until no further exotherm was noted. The reaction mixture wasstirred at -70° C. for 2.5 hours, warmed to room temperature, stirredovernight, and 10 ml isopropyl alcohol is added. The reaction mixturewas concentrated in vacuo and crystallized from ether/tetrahydrofuran togive a solid. The solid was added to 150 ml acetic acid and theresultant mixture was cooled to 20° C. A slurry of 20.5 g ofN-chlorosuccinimide in 125 ml acetic acid was added portionwise withcooling to maintain the reaction mixture between 20°-25° C. The reactionmixture was stirred 3 hours at ambient temperature and the solvent wasremoved under reduced pressure to give an oil. The oil was dissolved inmethylene chloride and washed with water. The organic phase was driedand the solvent removed under reduced pressure to give an oil which wasdissolved in 300 ml ether and cooled to 10° C. Excess ammonia (anhy.)was bubbled through the reaction mixture using ice bath cooling. Thereaction mixture was warmed to ambient temperature, stirred for 1 hour,and 100 ml ether added. The reaction mixture was washed with water,dried, and concentrated in vacuo to give a solid, m.p. 114°-117° C.,IR(mull).

¹ HNMR (DMSO-d₆): 4.3 (s, 4H); and 6.7-7.6 (m, 5H).

EXAMPLE 16N-[(4-Methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,4-benzodioxan-5-sulfonamide

To a solution of 1.0 g 1,4-benzodioxan-5-sulfonamide, prepared inExample 15, in 50 ml methylene chloride at ambient temperature undernitrogen was added 2.5 ml trimethylaluminum (2M in toluene). Afterstirring 15 minutes at ambient temperature, 1.0 g ofmethyl[4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared according tothe procedure of Example 3, was added and the reaction mixture washeated at reflux for 72 hours. The reaction mixture was cooled toambient temperature and 75 ml water, 10 ml glacial acetic acid and 10drops hydrochloric acid were sequentially added. The organic phase wasseparated, dried, and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from n-butyl chloride/ether gave asolid, m.p. 203°-205° C.

IR(mull) 1700 (c=o) cm⁻¹.

¹ HNMR ((CD₃)₂ CO): 2.5 (s, 3H), 4.0 (s, 3H); 4.4 (s, 3H); 6.4 (s, 1H);7.1 (m, 3H); and 7.7 (m, 2H).

EXAMPLE 17N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-benzodioxan-5-sulfonamide

To a solution of 1.0 g 1,4-benzodioxan-5-sulfonamide, prepared inExample 15, in 50 ml methylene chloride at ambient temperature undernitrogen, is added 2.5 ml trimethylaluminum (2M in toluene). Afterstirring 15 minutes at ambient temperature, 1.1 g ofmethyl[4,6-dimethoxytriazin-2-yl]carbamate, prepared in Example 5, isadded and the reaction mixture is heated at reflux 16 hours. Thereaction mixture is cooled to ambient temperature and 75 ml water, 10 mlglacial acetic acid, and 10 drops hydrochloric acid are sequentiallyadded. The organic phase is separated, dried and the solvent removedunder reduced pressure to give an oil. Crystallization of the oil froman appropriate organic solvent gives a solid.

EXAMPLE 18 1,4-Benzodithian-5-sulfonamide

To a solution of 17 g dibromo ethane and Aliquat 336® in 200 ml tolueneis added dropwise a solution of 22 g 3-bromothiocatechol [preparedaccording to the procedures of L. Horner et al., loc. cit. and A.Ferretti, loc. cit.,] 24 g of 50% sodium hydroxide, and 50 ml H₂ O. Thereaction mixture was then treated at reflux for 1.5 hour, cooled toambient temperature and stirred 16 hours. The organic phase wasseparated, washed with 1N sodium hydroxide and water, dried andconcentrated under reduced pressure to give an oil. The oil was purifiedvia distillation to give 15 g 4-bromo-1,3-benzodithiole. The oil wasdissolved in 60 ml of tetrahydrofuran under a nitrogen atmosphere,cooled to -70° C. and treated sequentially with 50 ml n-butyllithium(1.6N in hexanes) for 1 hour and excess sulfur dioxide until no furtherexotherm was noted. The reaction mixture was contacted with 3 mlisopropyl alcohol, concentrated in vacuo and crystallized fromether/tetrahydrofuran to give a solid. The solid was added to 150 mlacetic acid and cooled to 20° C. A slurry of 8.0 g N-chlorosuccinimidein 30 ml acetic acid was added portionwise with cooling to maintain areaction temperature of 20°-25° C. The reaction mixture was stirred forthree hours at room temperature and the solvent was removed underreduced pressure to give an oil which was dissolved in methylenechloride and washed with water. The organic phase was dried, and thesolvent removed under reduced pressure to give an oil which wasdissolved in 250 ml ether and cooled to 10° C. Excess ammonia (anhy.)was bubbled through the reaction mixture with external cooling. Thereaction mixture was washed with water, dried, and concentrated underreduced pressure to give a solid.

EXAMPLE 19N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-1,4-benzodithian-5-sulfonamide

To a solution of 2.5 g 1,4-benzodithian-5-sulfonamide, prepared inExample 18, in 50 ml methylene chloride at ambient temperature undernitrogen is added 5.5 ml trimethylaluminum (2M in toluene). Afterstirring 15 minutes at ambient temperature 2.0 g ofmethyl[4-methoxy-6-methylpyrimidin-2-yl]carbamate, prepared according tothe procedure of Example 3, is added and the reaction mixture is heatedat reflux for 16 hours. The reaction mixture is cooled to ambienttemperature and 75 ml water, 10 ml glacial acetic acid, and 10 dropshydrochloric acid are sequentially added. The organic phase isseparated, dried, and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from n-butyl chloride/ether gives asolid.

EXAMPLE 20N-[(4,6-Dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-benzodithian-5-sulfonamide

To a solution of 2.5 g 1,4-benzodithian-5-sulfonamide, prepared inExample 16, in 50 ml methylene chloride at ambient temperature undernitrogen is added 5.5 ml trimethylaluminum (2M in toluene). Afterstirring 15 minutes at ambient temperature 2.0 g ofmethyl[4,6-Dimethoxy-1,3,5-triazin-2-yl]carbamate, prepared according tothe procedure of Example 3 is added and the reaction mixture is heatedat reflux for 16 hours. The reaction mixture is cooled to ambienttemperature and 75 ml water, 10 ml glacial acetic acid, and 10 dropshydrochloric acid are sequentially added. The organic phase isseparated, dried and the solvent removed under reduced pressure to givean oil. Crystallization of the oil from an appropriate organic solventgives a solid.

The compounds of Table II can be prepared according to the procedures ofExamples 16, 17, 19 and 20 using the appropriate 5-sulfonamide andheterocyclic carbamate.

                                      TABLE Ia                                    __________________________________________________________________________     ##STR39##                                                                    W.sub.1                                                                           W   R.sub.1                                                                           R.sub.2    R.sub.7                                                                           X    Y       m.p. (°C.)                     __________________________________________________________________________    O   O   H   H          H   CH.sub.3                                                                           CH.sub.3                                      O   O   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   H          H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              O   O   H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   H          H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              O   O   H   H          H   OCH.sub.3                                                                          SCH.sub.3                                     O   O   H   H          H   OCH.sub.3                                                                          CH(OCH.sub.3).sub.2                           O   O   H   H          H   Cl   NH.sub.2                                      O   O   H   H          H   Cl   NHCH.sub.3                                    O   O   H   H          H   Cl   N(CH.sub.3)                                   O   O   H   H          H   Cl   OCH.sub.3                                     O   O   H   H          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      O   O   H   H          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      O   O   H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3   H   CH.sub.3                                                                           SCH.sub.3                                     O   O   H   CH.sub.3   H   CH.sub.3                                                                           CH(OCH.sub.3).sub.2                           O   O   H   CH.sub.3   H   OCH.sub.3                                                                          CH.sub.3                                      O   O   H   CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub.3   H   OCH.sub.3                                                                           ##STR40##                                    O   O   H   CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             O   O   H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           NH.sub.2                                      O   O   H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              O   O   H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           SCH.sub.3                                     O   O   H   C.sub.2 H.sub.5                                                                          H   OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                            O   O   H   C.sub.2 H.sub.5                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub. 3 CH.sub.2 CH.sub.2                                                              H   CH.sub.3                                                                           N(CH.sub.3).sub.2                             O   O   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          NH.sub.2                                      O   O   H   CH(CH.sub.3).sub.2                                                                       H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   CH.sub.3                                                                           NH(CH.sub.3)                                  O   O   H   CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              O   O   H   (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   (CH.sub.3).sub.3 C                                                                       H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           H                                             O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                                                              168-171°                       O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                                                             180-183°                       O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           SCH.sub. 3                                    O   O   CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                                                             194-203°                       O   O   CH.sub.3                                                                          CH.sub.3   H   Cl   OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3   H   Cl   NH.sub.2                                      O   O   CH.sub.3                                                                          CH.sub.3   H   Cl   NH(CH.sub.3)                                  O   O   CH.sub.3                                                                          CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             O   O   CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      O   O   CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           CH.sub.3                                      O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                            ##STR41##                                    O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OC.sub.2 H.sub. 5                             O   O   CH.sub.3                                                                          (CH.sub.3).sub.2 CH                                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           N(CH.sub.3).sub.2                             O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   Cl   N(CH.sub.3).sub.2                             O   O   CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   CH.sub.3                                                                           NHCH.sub.3                                    O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           CH(OCH.sub.3).sub.2                           S   S   H   H          H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   H          H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              S   S   H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   H          H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              S   S   H   H          H   OCH.sub.3                                                                          SCH.sub.3                                     S   S   H   H          H   OCH.sub.3                                                                          CH(OCH.sub. 3).sub.2                          S   S   H   H          H   Cl   NH.sub.2                                      S   S   H   H          H   Cl   NHCH.sub.3                                    S   S   H   H          H   Cl   N(CH.sub.3).sub.2                             S   S   H   H          H   Cl   OCH.sub.3                                     S   S   H   H          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      S   S   H   H          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH.sub.3   H   CH.sub.3                                                                           N(CH.sub.3).sub.2                             S   S   H   CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   CH.sub.3   H   OCH.sub.3                                                                           ##STR42##                                    S   S   H   CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             S   S   H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           SCH.sub.3                                     S   S   H   C.sub.2 H.sub.5                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub. 3                                                                          CH.sub.3                                      S   S   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH(CH.sub.3).sub.2                                                                       H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   (CH.sub.3).sub.3 C                                                                       H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           H                                             S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           SCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                           ##STR43##                                    S   S   CH.sub.3                                                                          CH.sub.3   H   Cl   OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   H   Cl   NH.sub.2                                      S   S   CH.sub.3                                                                          CH.sub.3   H   Cl   NH(CH.sub.3)                                  S   S   CH.sub.3                                                                          CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             S   S   CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           CH.sub.3                                      S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          CH(OCH.sub.3).sub.2                           S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH(OCH.sub.3).sub.2                           S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              S   S   CH.sub. 3                                                                         (CH.sub.3).sub.2 CH                                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           SCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   Cl   N(CH.sub.3).sub.2                             S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          SCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          CH(OCH.sub.3).sub.2                           SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   Cl   N(CH.sub. 3).sub.2                            SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   Cl   OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   H          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           SCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           H                                             SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                                                             191-200°                       SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          SCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   Cl   OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   Cl   NH.sub.2                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   Cl   NH(CH.sub.3)                                  SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          CH(OCH.sub.3).sub.2                           SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          H                                             SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CH                                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           SCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   OCH.sub.3                                                                          H                                             SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   Cl   N(CH.sub.3).sub.2                             SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   Cl   N(CH.sub.3).sub.2                             SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             SO.sub.2                                                                          SO.sub.2                                                                          H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   C.sub.2 H.sub.5                                                                          H   CH.sub.3                                                                           SCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   C.sub.2 H.sub.5                                                                          H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH(CH.sub.3).sub.2                                                                       H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   (CH.sub.3).sub.3 C                                                                       H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   H          H   CH.sub.3                                                                           CH.sub.3                                      SO  SO  H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   H          H   OCH.sub.3                                                                          SCH.sub.3                                     SO  SO  H   H          CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      SO  SO  H   H          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      SO  SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                     SO  SO  CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     O   S   H   H          H   CH.sub.3                                                                           CH.sub.3                                      O   S   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   S   H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     O   SO  H   H          H   CH.sub.3                                                                           CH.sub.3                                      O   SO  H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   SO  H   CH.sub.3   H   CH.sub.3                                                                           SCH.sub.3                                     O   SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      O   SO  CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     O   SO  CH.sub.3                                                                          CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             O   SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           CH.sub.3                                      O   SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          H   H          H   Cl   N(CH.sub.3).sub.2                             O   SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      O   SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           CH(OCH.sub.3).sub.2                           O   SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      O   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          SCH.sub.3                                     O   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     S   O   H   H          H   CH.sub. 3                                                                          OCH.sub.3                                     S   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  O   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO  O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          O   H   H          H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  S   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO  S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          S   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   SO  H   H          H   CH.sub.3                                                                           OCH.sub.3                                     S   SO  H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           CH.sub.3                                      S   SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     S   SO.sub.2                                                                          H   CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     S   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     SO  SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO.sub.2                                                                          CH.sub.3                                                                          CH.sub. 3  H   CH.sub.3                                                                           CH.sub.3                                      SO  SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   Cl   N(CH.sub.3).sub.2                             SO.sub.2                                                                          SO  H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO  H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO  H   CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     S   SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     __________________________________________________________________________

                                      TABLE Ib                                    __________________________________________________________________________     ##STR44##                                                                    W.sub.1                                                                           W   R.sub.1                                                                           R.sub.2    R.sub.7                                                                           X    Y       m.p. (°C.)                     __________________________________________________________________________    O   O   H   H          H   CH.sub.3                                                                           CH.sub.3                                      O   O   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   H          H   CH.sub.3                                                                           SCH.sub.3                                     O   O   H   H          H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              O   O   H   H          H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            O   O   H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   H          H   OCH.sub.3                                                                          N(CH.sub.3).sub.2                             O   O   H   H          H   OCH.sub.3                                                                          SCH.sub.3                                     O   O   H   H          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub. 3                                    O   O   H   H          CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      O   O   H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub.3   H   OCH.sub.3                                                                          NH(CH.sub.3)                                  O   O   H   CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                           ##STR45##                                    O   O   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      O   O   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          CH.sub.2 OCH.sub.3                            O   O   H   (CH.sub.3).sub.2 CH                                                                      H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      O   O   H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   H   CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     O   O   H   (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                                                              168-171°                       O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                                                             160-168°                       O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           SCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            O   O   CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                                                             194-202°                       O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.2                                                                           OC.sub.2 H.sub.5                              O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           SCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          (CH.sub.3).sub.2 CH                                                                      H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           SCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 (CH.sub.3)CH.sub.2                                                              H   OCH.sub.3                                                                          OCH.sub.3                                     O   O   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     O   O   CH.sub.3                                                                          (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   H          H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   H          H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              S   S   H   H          H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            S   S   H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   H          H   OCH.sub.3                                                                          SCH.sub.3                                     S   S   H   H          H   OCH.sub.3                                                                          CH(OCH.sub.3).sub.2                           S   S   H   H          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     S   S   H   H          CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   CH.sub. 3  H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              S   S   H   CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              S   S   H   CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                           ##STR46##                                    S   S   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                            ##STR47##                                    S   S   H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   (CH.sub.3).sub.2 CH                                                                      H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      S   S   H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   H   CH.sub.3 CH.sub.2 CH(CH.sub.3 )                                                          H   CH.sub.3                                                                           OCH.sub.3                                     S   S   H   (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              S   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            S   S   CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      S   S   CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           SCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          (CH.sub.3).sub.2 CH                                                                      H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   OCH.sub.3                                                                          OCH.sub.3                                     S   S   CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     S   S   CH.sub.3                                                                          (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          SCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          H   OCH.sub.3                                                                          CH(OCH.sub.3).sub.2                           SO.sub.2                                                                          SO.sub.2                                                                          H   H          CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   H          CH.sub.3                                                                          OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub. 2                                                                         SO.sub.2                                                                          H   CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3   H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2                                                                        H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.2 H.sub.5                             SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                           ##STR48##                                    SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   (CH.sub.3).sub.2 CH                                                                      H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          H   (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OC.sub.2 H.sub.5                              SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.2 OCH.sub.3                            SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   CH.sub.3                                                                          CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   CH.sub.2                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2                                                                        H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub. 2                                                                         CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   CH.sub.3                                                                           SCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2                                                               H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          (CH.sub.3).sub.2 CH                                                                      H   CH.sub.2                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           CH.sub.3                                      SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H   OCH.sub.3                                                                          OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3 CH.sub.2 CH(CH.sub.3)                                                           H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO.sub.2                                                                          CH.sub.3                                                                          (CH.sub.3).sub.3 C                                                                       H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   H          H   CH.sub.3                                                                           CH.sub.3                                      SO  SO  H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  H   CH.sub.3   H   CH.sub.3                                                                           SCH.sub.3                                     SO  SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      SO  SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           SCH.sub.3                                     SO  SO  CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     SO  SO  CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OC.sub.2 H.sub.5                              O   S   H   H          H   CH.sub.3                                                                           CH.sub.3                                      O   S   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   S   H   H          H   OCH.sub.3                                                                          OCH.sub.3                                     O   S   H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      O   S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   S   CH.sub.3                                                                          CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     O   SO  H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   SO  H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           CH.sub.3                                      O   SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     O   SO.sub.2                                                                          CH.sub. 3                                                                         CH.sub.3   H   OCH.sub.3                                                                          OCH.sub.3                                     S   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           CH.sub.3                                      S   O   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          O   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          O   CH.sub.3                                                                          H          H   CH.sub.3                                                                           OCH.sub.3                                     SO  S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          S   H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          S   CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   SO  H   H          H   CH.sub.3                                                                           OCH.sub.3                                     S   SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     S   SO.sub.2                                                                          H   CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     S   SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO.sub.2                                                                          SO  CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO.sub.2                                                                          H   H          H   CH.sub.3                                                                           OCH.sub.3                                     SO  SO.sub.2                                                                          CH.sub.3                                                                          CH.sub.3   H   CH.sub.3                                                                           OCH.sub.3                                     __________________________________________________________________________

                  TABLE Ic                                                        ______________________________________                                         ##STR49##                                                                                                             m.p.                                 W.sub.1                                                                            W      R.sub.1                                                                              R.sub.2    R.sub.7                                                                            G     X.sub.1   (°C.)               ______________________________________                                        O    O      H      H          H    O     CH.sub.3                             O    O      H      H          H    O     OCH.sub.3                            O    O      H      H          H    CH.sub.2                                                                            CH.sub.3                             O    0      H      H          CH.sub.3                                                                           CH.sub.2                                                                            CH.sub.3                             O    O      H      H          CH.sub.3                                                                           O     CH.sub.3                             O    O      H      H          CH.sub.3                                                                           O     OCH.sub.3                            O    O      H      CH.sub.3   H    O     CH.sub.3                             O    O      H      CH.sub.3   H    O     OCH.sub.3                            O    O      H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.2                                                                            OCH.sub.3                            O    O      H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    O     OCH.sub.3                            O    O      H      (CH.sub.3).sub.2 CH                                                                      H    O     OCH.sub.3                            O    O      H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    O     OCH.sub.3                            O    O      H      CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.2                                                                            CH.sub.3                             O    O      H      (CH.sub.3).sub.3 C                                                                       H    O     CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3   H    O     OCH.sub.3                            O    O      CH.sub.3                                                                             CH.sub.3   H    CH.sub.2                                                                            CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3   H    CH.sub.2                                                                            OCH.sub.3                            O    O      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.2                                                                            CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           O     CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           O     OCH.sub.3                            O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    O     CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    O     CH.sub.3                             O    O      CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    O     CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    O     CH.sub.3                             O    O      CH.sub.3                                                                             CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    O     CH.sub.3                             O    O      CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    O     CH.sub.3                             S    S      H      H          H    O     CH.sub.3                             S    S      H      H          H    O     OCH.sub.3                            S    S      H      H          H    CH.sub.2                                                                            CH.sub.3                             S    S      H      H          CH.sub.3                                                                           CH.sub.2                                                                            CH.sub.3                             S    S      H      H          CH.sub.3                                                                           O     CH.sub.3                             S    S      H      H          CH.sub.3                                                                           O     OCH.sub.3                            S    S      H      CH.sub.3   H    O     CH.sub.3                             S    S      H      CH.sub.3   H    O     OCH.sub.3                            S    S      H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.2                                                                            CH.sub.3                             S    S      H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    O     OCH.sub.3                            S    S      H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    O     OCH.sub.3                            S    S      CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             S    S      CH.sub.3                                                                             CH.sub.3   H    O     OCH.sub.3                            S    S      CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                                                           CH.sub.3                             S    S      CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                                                           OCH.sub.3                            S    S      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.2                                                                            CH.sub.3                             S    S      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           O     CH.sub.3                             S    S      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           O     OCH.sub.3                            S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    O     CH.sub.3                             S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    O     CH.sub.3                             S    S      CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    O     CH.sub.3                             S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    O     CH.sub.3                             S    S      CH.sub.3                                                                             CH.sub.3 CH(CH.sub.3)CH.sub.2                                                            H    O     CH.sub.3                             S    S      CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    O     OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    CH.sub.2                                                                            CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    CH.sub.2                                                                            OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             H      H          CH.sub.3                                                                           CH.sub.2                                                                            CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             H      H          CH.sub.3                                                                           O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             H      H          CH.sub.3                                                                           O     OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3   H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3   H    O     OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.2                                                                            OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2 CH.sub.3                                                               H    CH.sub.2                                                                            OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2 CH.sub.3                                                               H    O     OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    O     OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.2                                                                            CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.2                                                                            OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.2                                                                            CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           O     OCH.sub.3                            SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH(CH.sub. 3)CH.sub.2                                                           H    O     CH.sub.3                             SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    O     CH.sub.3                             SO   SO     H      H          H    CH.sub.2                                                                            CH.sub.3                             SO   SO     H      H          H    O     OCH.sub.3                            SO   SO     CH.sub.3                                                                             CH.sub.3   H    CH.sub.2                                                                            CH.sub.3                             SO   SO     CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             O    S      H      H          H    O     CH.sub.3                             O    S      CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             O    SO     H      H          H    O     CH.sub.3                             O    SO     CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             O    SO.sub.2                                                                             H      H          H    O     CH.sub.3                             O    SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             S    O      H      H          H    O     CH.sub.3                             SO   O      H      H          H    O     CH.sub.3                             SO.sub.2                                                                           O      H      H          H    O     CH.sub.3                             SO   S      CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             SO.sub.2                                                                           S      H      H          H    O     CH.sub.3                             SO.sub.2                                                                           S      CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             S    SO     CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             S    SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    O     CH.sub.3                             SO.sub.2                                                                           SO     H      H          H    O     CH.sub. 3                            SO   SO.sub.2                                                                             H      H          H    O     CH.sub.3                             ______________________________________                                    

                  TABLE Id                                                        ______________________________________                                         ##STR50##                                                                    W.sub.1                                                                            W      R.sub.1                                                                              R.sub.2    R.sub.7                                                                            X.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        O    O      H      H          H    CH.sub.3                                   O    O      H      H          H    OCH.sub.3                                  O    O      H      H          CH.sub.3                                                                           CH.sub.3                                   O    O      H      H          CH.sub.3                                                                           OCH.sub.3                                  O    O      H      CH.sub.3   H    CH.sub.3                                   O    O      H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   O    O      H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   O    O      H      (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   O    O      H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   O    O      H      CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   O    O      H      (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  O    O      CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           OCH.sub.3                                  O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   O    O      CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    CH                                         O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   O    O      CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   S    S      H      H          H    CH.sub.3                                   S    S      H      H          H    OCH.sub.3                                  S    S      H      H          CH.sub.3                                                                           CH.sub.3                                   S    S      H      H          CH.sub.3                                                                           OCH.sub.3                                  S    S      H      CH.sub.3   H    CH.sub.3                                   S    S      H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   S    S      H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   S    S      H      (CH.sub.3).sub. 2 CH                                                                     H    CH.sub.3                                   S    S      H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   S    S      H      CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   S    S      H      (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  S    S      CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           OCH.sub.3                                  S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   S    S      CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   S    S      CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             H      H          CH.sub.3                                                                           CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      H          CH.sub.3                                                                           OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub. 3  H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3   H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub. 3                                  SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 (CH.sub.3)CH.sub.3                                                              H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   SO   SO     CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   SO   SO     CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  O    S      H      H          H    CH.sub.3                                   O    SO     CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   O    SO     CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   O    SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   S    O      H      H          H    CH.sub.3                                   SO   O      H      H          H    CH.sub.3                                   SO.sub.2                                                                           O      H      H          H    CH.sub.3                                   SO   S      H      H          H    CH.sub.3                                   S    SO.sub.2                                                                             H      H          H    CH.sub.3                                   S    SO     H      H          H    CH.sub.3                                   S    SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   SO.sub.2                                                                           SO     H      H          H    CH.sub.3                                   SO   SO.sub.2                                                                             H      H          H    CH.sub.3                                   ______________________________________                                    

                  TABLE Ie                                                        ______________________________________                                         ##STR51##                                                                    W.sub.1                                                                            W      R.sub.1                                                                              R.sub.2    R.sub.7                                                                            X.sub.1                                                                             m.p. (°C.)                    ______________________________________                                        O    O      H      H          H    CH.sub.3                                   O    O      H      H          H    OCH.sub.3                                  O    O      H      H          CH.sub.3                                                                           CH.sub.3                                   O    O      H      H          CH.sub.3                                                                           OCH.sub.3                                  O    O      H      CH.sub.3   H    CH.sub.3                                   O    O      H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   O    O      H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   O    O      H      (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   O    O      H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   O    O      H      CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   O    O      H      (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  O    O      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           OCH.sub.3                                  O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   O    O      CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   O    O      CH.sub.3                                                                             CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   O    O      CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   S    S      H      H          H    CH.sub.3                                   S    S      H      H          H    OCH.sub.3                                  S    S      H      H          CH.sub.3                                                                           CH.sub.3                                   S    S      H      H          CH.sub.3                                                                           OCH.sub.3                                  S    S      H      CH.sub.3   H    CH.sub.3                                   S    S      H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   S    S      H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   S    S      H      (CH.sub.3).sub.2 CH                                                                      H    CH.sub. 3                                  S    S      H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   S    S      H      CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   S    S      H      (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  S    S      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           OCH.sub.3                                  S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   S    S      CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   S    S      CH.sub.3                                                                             CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   S    S      CH.sub.3                                                                             (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      H          H    OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             H      H          CH.sub.3                                                                           CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      H          CH.sub.3                                                                           OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3   H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             H      (CH.sub.3).sub.3 C                                                                       H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   CH.sub.3                                                                           OCH.sub.3                                  SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2                                                                        H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2                                                               H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             (CH.sub.3).sub.2 CH                                                                      H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                      H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3 CH(CH.sub.3)CH.sub.3                                                            H    CH.sub.3                                   SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             (CH.sub.3 ).sub.3 C                                                                      H    CH.sub.3                                   SO   SO     CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   SO   SO     CH.sub.3                                                                             CH.sub.3   H    OCH.sub.3                                  O    S      H      H          H    CH.sub.3                                   O    SO     CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   O    SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   S    O      H      H          H    CH.sub.3                                   SO   O      H      H          H    CH.sub.3                                   SO.sub.2                                                                           O      H      H          H    CH.sub.3                                   SO   S      H      H          H    CH.sub.3                                   S    SO.sub.2                                                                             H      H          H    CH.sub.3                                   S    SO     H      H          H    CH.sub.3                                   S    SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3   H    CH.sub.3                                   SO.sub.2                                                                           SO     H      H          H    CH.sub.3                                   SO   SO.sub.2                                                                             H      H          H    CH.sub.3                                   ______________________________________                                    

                  TABLE If                                                        ______________________________________                                         ##STR52##                                                                                                              m.p.                                W.sub.1                                                                            W      R.sub.1 R.sub.2 R.sub.7 X.sub.2                                                                         Y.sub.2                                                                           (°C.)                        ______________________________________                                        O    O      HH              HCH.sub.3  OCH.sub.3                              O    O      HH              HCH.sub.3 CH.sub.2                                                                       SCH.sub.3                              O    O      HH              HCH.sub.2 CF.sub.3                                                                       OCH.sub.3                              O    O      HH              CH.sub.3 CH.sub.3                                                                        OCH.sub.3                              O    O      HCH.sub.3       HCH.sub.3 CH.sub.2 CH.sub.2                                                              OC.sub.2 H.sub.5                       O    O      HCH.sub.3 CH.sub.2                                                                            H(CH.sub.3).sub.2 CH                                                                     SC.sub.2 H.sub.5                       O    O      HCH.sub.3 CH.sub.2 CH.sub.2                                                                   HCH.sub.3  OCH.sub.3                              O    O      H(CH.sub. 3).sub.2 CH                                                                         HCH.sub.3  OCH.sub.3                              O    O      HCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                          HCH.sub.3  OCH.sub.3                              O    O      HCH.sub.3 CH(CH.sub.3).sub.2 CH.sub.2                                                         HCH.sub.3  OCH.sub.3                              O    O      H(CH.sub.3).sub.3 C                                                                           HCH.sub.3  OCH.sub.3                              O    O      CH.sub.3 CH.sub.3                                                                             HCH.sub.3  OCH.sub.3                              O    O      CH.sub.3 CH.sub.3                                                                             HCH.sub.3  SCH.sub.3                              O    O      CH.sub.3 CH.sub.3                                                                             HCH.sub.3 CH.sub.2                                                                       OCH.sub.3                              O    O      CH.sub.3 CH.sub.3                                                                             HCH.sub.2 CF.sub.3                                                                       OCH.sub.3                              O    O      CH.sub.3 CH.sub.3                                                                             HCH.sub.2 CF.sub.3                                                                       SCH.sub.3                              O    O      CH.sub.3 CH.sub.3                                                                             CH.sub.3 CH.sub.3                                                                        OCH.sub.3                              O    O      CH.sub.3 CH.sub.3 CH.sub.2                                                                    HCH.sub.3  OCH.sub.3                              O    O      CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2                                                           HCH.sub.3  OCH.sub.3                              O    O      CH.sub.3 (CH.sub.3).sub.2 CH                                                                  HCH.sub.3  OCH.sub.3                              O    O      CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                  HCH.sub.3  OCH.sub.3                              O    O      CH.sub.3 CH.sub.3 CH(CH.sub.3)CH.sub.2                                                        HCH.sub.3  OCH.sub. 3                             O    O      CH.sub.3 (CH.sub.3).sub.3 C                                                                   HCH.sub.3  OCH.sub.3                              S    S      HH              HCH.sub.3  OCH.sub.3                              S    S      HH              HCH.sub.3 CH.sub.2                                                                       SCH.sub.3                              S    S      HH              HCH.sub.2 CF.sub.3                                                                       OCH.sub.3                              S    S      HH              CH.sub.3 CH.sub.3                                                                        OCH.sub.3                              S    S      HCH.sub.3       HCH.sub.3 CH.sub.2 CH.sub.2                                                              OC.sub.2 H.sub.5                       S    S      HCH.sub.3 CH.sub.2                                                                            H(CH.sub.3).sub.2 CH                                                                     SC.sub.2 H.sub.5                       S    S      HCH.sub.3 CH.sub.2 CH.sub.2                                                                   HCH.sub.3  OCH.sub.3                              S    S      H(CH.sub.3).sub.2 CH                                                                          HCH.sub.3  OCH.sub.3                              S    S      HCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                          HCH.sub.3  OCH.sub.3                              S    S      HCH.sub.3 CH(CH.sub.3).sub.2 CH.sub.2                                                         HCH.sub.3  OCH.sub.3                              S    S      H(CH.sub.3).sub.3 C                                                                           HCH.sub.3  OCH.sub.3                              S    S      CH.sub.3 CH.sub.3                                                                             HCH.sub.3  OCH.sub.3                              S    S      CH.sub.3 CH.sub.3                                                                             HCH.sub.3  SCH.sub.3                              S    S      CH.sub.3 CH.sub.3                                                                             HCH.sub.3 CH.sub.2                                                                       OCH.sub.3                              S    S      CH.sub.3  CH.sub.3                                                                            HCH.sub.2 CF.sub.3                                                                       OCH.sub.3                              S    S      CH.sub.3 CH.sub.3                                                                             HCH.sub.2 CF.sub.3                                                                       SCH.sub.3                              S    S      CH.sub.3 CH.sub.3                                                                             CH.sub.3 CH.sub.3                                                                        OCH.sub.3                              S    S      CH.sub.3 CH.sub.3 CH.sub.2                                                                    HCH.sub.3  OCH.sub.3                              S    S      CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2                                                           HCH.sub.3  OCH.sub.3                              S    S      CH.sub.3 (CH.sub.3).sub.2 CH                                                                  HCH.sub.3  OCH.sub.3                              S    S      CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                  HCH.sub.3  OCH.sub.3                              S    S      CH.sub.3 CH.sub.3 CH(CH.sub.3)CH.sub.2                                                        HCH.sub.3  OCH.sub.3                              S    S      CH.sub.3 (CH.sub.3).sub.3 C                                                                   HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             HH              HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             HH              HCH.sub.3 CF.sub.2                                                                       SCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             HH              HCH.sub.2 CH.sub.3                                                                       OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             HH              CH.sub.3 CH.sub.3                                                                        OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             HCH.sub.3       HCH.sub.3 CH.sub.2 CH.sub.2                                                              OC.sub.2 H.sub.5                       SO.sub.2                                                                           SO.sub.2                                                                             HCH.sub.3 CH.sub.2                                                                            H(CH.sub. 3).sub.2 CH                                                                    SC.sub.2 H.sub.5                       SO.sub.2                                                                           SO.sub.2                                                                             HCH.sub.3 CH.sub.2 CH.sub.2                                                                   HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             H(CH.sub.3).sub.2 CH                                                                          HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             HCH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                          HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             HCH.sub.3 CH(CH.sub.3).sub.2 CH.sub.2                                                         HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             H(CH.sub.3).sub.3 C                                                                           HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             HCH.sub.3  SCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             HCH.sub.3 CH.sub.2                                                                       OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             HCH.sub.2 CF.sub.3                                                                       OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             HCH.sub.2 CF.sub.3                                                                       SCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             CH.sub.3 CH.sub.3                                                                        OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3 CH.sub.2                                                                    HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2                                                           HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 (CH.sub.3).sub.2 CH                                                                  HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CH.sub.2                                                  HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 CH.sub.3 CH(CH.sub.3)CH.sub.2                                                        HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3 (CH.sub.3).sub.3 C                                                                   HCH.sub.3  OCH.sub.3                              SO   SO     HH              HCH.sub.3  OCH.sub.3                              SO   SO     CH.sub.3 CH.sub.3                                                                             HCH.sub.3  SCH.sub.3                              O    S      HH              HCH.sub.3  OCH.sub.3                              O    SO     CH.sub.3 CH.sub.3                                                                             HCH.sub.3  OCH.sub.3                              O    SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             HCH.sub.3  OCH.sub.3                              S    O      HH              HCH.sub.3  OCH.sub.3                              SO   O      HH              HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           O      HH              HCH.sub.3  OCH.sub.3                              S    SO     HH              HCH.sub.3  OCH.sub.3                              S    SO.sub.2                                                                             HH              HCH.sub.3  OCH.sub.3                              S    SO     HH              HCH.sub.3  OCH.sub.3                              S    SO.sub.2                                                                             CH.sub.3 CH.sub.3                                                                             HCH.sub.3  OCH.sub.3                              SO.sub.2                                                                           SO     HH              HCH.sub.3  OCH.sub.3                              SO   SO.sub.2                                                                             HH              HCH.sub.3  OCH.sub.3                              ______________________________________                                    

                  TABLE IIa                                                       ______________________________________                                         ##STR53##                                                                                                            m.p.                                  W.sub.1 WR.sub.3                                                                       R.sub.4 R.sub.5 R.sub.6                                                                   R.sub.7 X Y        (°C.)                          ______________________________________                                        OOH      HHH         HCH.sub.3 CH.sub.3                                       OOH      HHH         HCH.sub.3 OCH.sub.3                                                                              203-                                                                          205°                           OOH      HHH         HCH.sub.3 SCH.sub.3                                      OOH      HHH         HCH.sub.3 NH.sub.2                                       OOH      HHH         HOCH.sub.3                                                                              OCH.sub.3                                      OOH      HHH         HOCH.sub.3                                                                              CH.sub.2 OCH.sub.3                             OO H     HHH         HOCH.sub.3                                                                              CH(OCH.sub.3).sub.2                            OOH      HHH         HCl       OCH.sub.3                                      OOH      HHH         HCl       NH.sub.2                                       OOH      HHH         HCl       NH(CH.sub.3)                                   OOH      HHH         HCl       N(CH.sub.3).sub.2                              OOH      HHH         CH.sub.3 CH.sub.3                                                                       CH.sub.3                                       OOH      HHH         CH.sub.3 CH.sub.3                                                                       OCH.sub.3                                      OOCH.sub.3                                                                             HHH         HCH.sub.3 CH.sub.3                                       OOCH.sub.3                                                                             HHH         HCH.sub.3 OCH.sub.3                                      OOCH.sub.3                                                                             HHH         HOCH.sub.3                                                                              OCH.sub.3                                      OOCH.sub.3                                                                             HHH         HOCH.sub.3                                                                              CH.sub.2 (OCH.sub.3)                           OOCH.sub.3                                                                             HHH         HCl       N(CH.sub.3).sub.2                              OOCH.sub.3                                                                             HCH.sub.3 H HCH.sub.3 CH.sub.3                                       OOCH.sub.3                                                                             HCH.sub.3 H HCH.sub.3 OC.sub.2 H.sub.5                               OOCH.sub.3                                                                             HCH.sub.3 H HCH.sub.3 CH.sub.3 (OCH.sub.3).sub.2                     OOCH.sub.3                                                                             HCH.sub.3 H HOCH.sub.3                                                                              OCH.sub.3                                      OOCH.sub.3                                                                             CH.sub.3 HH HCH.sub.3 CH.sub.3                                       OOCH.sub.3                                                                             CH.sub.3 HH HCH.sub.3 OCH.sub.3                                      OOCH.sub.3                                                                             CH.sub.3 HH HOCH.sub.3                                                                              OC.sub.2 H.sub.5                               OOCH.sub.3                                                                             CH.sub.3 HH HCl       N(CH.sub.3).sub.2                              OOCH.sub.3                                                                             CH.sub.3 CHH                                                                              HCH.sub.3 CH.sub.3                                       OOCH.sub.3                                                                             CH.sub.3 CH.sub.3 H                                                                       HOCH.sub.3                                                                              SCH.sub.3                                      OOCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HOCH.sub.3                                                                              OCH.sub.3                                      OOCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HCH.sub.3 CH(OCH.sub.3).sub.2                            OOCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HH                                                                                       ##STR54##                                     OOCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HOCH.sub.3                                                                              SCH.sub.3                                      OOCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                CH.sub.3 CH.sub.3                                                                       CH.sub.3                                       OOCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                CH.sub.3 CH.sub.3                                                                       OCH.sub.3                                      O OCH.sub.3                                                                            CH.sub.3 CH.sub.3 CH.sub.3                                                                CH.sub.3 OCH.sub.3                                                                      OCH.sub.3                                      SOH      HHH         HCH.sub.3 CH.sub.3                                       SSH      HHH         HCH.sub.3 OCH.sub.3                                      SSH      HHH         HCH.sub.3 N(CH.sub.3).sub.2                              SSH      HHH         HOCH.sub.3                                                                              H                                              SSH      HHH         HOCH.sub.3                                                                              OCH.sub.3                                      SSH      HHH         HOCH.sub.3                                                                              CH.sub.3 (OCH.sub.3).sub.2                     SSH      HHH         HCl       OCH.sub.3                                      SSH      HHH         HCl       NH.sub.2                                       SSH      HHH         HCl       N(CH.sub.3).sub.2                              SSH      HHH         CH.sub.3 CH.sub.3                                                                       OCH.sub.3                                      SSH      HHH         CH.sub.3 OCH.sub.3                                                                      OCH.sub.3                                      SSCH.sub.3                                                                             HHH         HCH.sub.3                                                                                ##STR55##                                     SSCH.sub.3                                                                             HHH         HCH.sub.3 OCH.sub.3                                      SSCH.sub.3                                                                             HHH         HOCH.sub.3                                                                              OCH.sub.3                                      S SCH.sub.3                                                                            HHH         HCl       OCH.sub.3                                      SSCH.sub.3                                                                             HHH         HCl       N(CH.sub.3).sub.2                              SSCH.sub.3                                                                             HCH.sub.3 H HCH.sub.3 CH.sub.3                                       SSCH.sub.3                                                                             HCH.sub.3 H HCH.sub.3 OCH.sub.3                                      SSCH.sub.3                                                                             HCH.sub.3 H HCH.sub.3 OCH.sub.3                                      SSCH.sub.3                                                                             HCH.sub.3 H HOCH.sub.3                                                                               ##STR56##                                     SSCH.sub.3                                                                             CH.sub.3 HH HCH.sub.3 CH.sub.3                                       SSCH.sub.3                                                                             CH.sub.3 HH HCH.sub.3 OCH.sub.3                                      SSCH.sub.3                                                                             CH.sub.3 HH HOCH.sub.3                                                                              OCH.sub.3                                      SSCH.sub.3                                                                             CH.sub.3 HH HOCH.sub.3                                                                              N(CH.sub.3).sub.2                              SSCH.sub.3                                                                             CH.sub.3 CH.sub.3 H                                                                       HCH.sub.3 CH.sub.3                                       SSCH.sub.3                                                                             CH.sub.3 CH.sub.3 H                                                                       HOCH.sub.3                                                                              NH.sub.2                                       SSCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HOCH.sub.3                                                                              OCH.sub.3                                      SSCH.sub.3                                                                             CH.sub.3 CH.sub. 3 CH.sub.3                                                               HCH.sub.3 CH(OCH.sub.3).sub.2                            SSCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HCH.sub.3                                                                                ##STR57##                                     SSCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HOCH.sub.3                                                                              SCH.sub.3                                      SSCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                CH.sub.3 CH.sub.3                                                                       CH.sub.3                                       SSCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                CH.sub.3 CH.sub.3                                                                       OCH.sub.3                                      SO.sub.2 SO.sub.2 H                                                                    HHH         HCH.sub.3 CH.sub.3                                       SO.sub.2 SO.sub.2 H                                                                    HHH         HCH.sub.3 NHCH.sub.3                                     SO.sub.2 SO.sub.2 H                                                                    HHH         HCH.sub.3 OCH.sub.3                                      SO.sub.2 SO.sub.2 H                                                                    HHH         HCH.sub.3 SCH.sub.3                                      SO.sub.2 SO.sub.2 H                                                                    HHH         HOCH.sub.3                                                                              H                                              SO.sub.2 SO.sub.2 H                                                                    HHH         HOCH.sub.3                                                                              OCH.sub.3                                      SO.sub.2 SO.sub.2 H                                                                    HHH         HOCH.sub.3                                                                              CH.sub.2 (OCH.sub.3).sub.2                     SO.sub.2 SO.sub.2 H                                                                    HHH         HOCH.sub.3                                                                              NH(CH.sub.3 ).sub.2                            SO.sub.2 SO.sub.2 H                                                                    HHH         HCl       OCH.sub.3                                      SO.sub.2 SO.sub.2 H                                                                    HHH         HCl       NH.sub.2                                       SO.sub.2 SO.sub.2 H                                                                    HHH         HCl       N(CH.sub.3).sub.2                              SO.sub.2 SO.sub.2 H                                                                    HHH         CH.sub.3 CH.sub.3                                                                       OCH.sub.3                                      SO.sub.2 SO.sub.2 H                                                                    HHH         CH.sub.3 OCH.sub.3                                                                      OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             HHH         HCH.sub.3 CH.sub.3                                       SO.sub.2 SO.sub.2 CH.sub.3                                                             HHH         HCH.sub.3 OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             HHH         HOCH.sub.3                                                                              OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             HHH         HCl       OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             HHH         HCl       N(CH.sub.3).sub.2                              SO.sub.2 SO.sub.2 CH.sub.3                                                             HCH.sub.3 H HCH.sub.3 CH.sub.3                                       SO.sub.2 SO.sub.2 CH.sub.3                                                             HCH.sub.3 H HCH.sub.3 OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             HCH.sub.3 H HOCH.sub.3                                                                              OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 HH HCH.sub.3 CH.sub.3                                       SO.sub.2 CH.sub.3 HHH.sub.3                                                                        HCH.sub.3 NH(CH.sub.3)                                   SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 HH HOCH.sub.3                                                                              OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 HH HOCH.sub.3                                                                              N(CH.sub.3).sub.2                              SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 CH.sub.3 H                                                                       HCH.sub.3 CH.sub.3                                       SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 CH.sub.3 H                                                                       HOCH.sub.3                                                                              OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HOCH.sub.3                                                                              OCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HCH.sub.3 CH(OCH.sub.3).sub.2                            SO.sub.2 SO.sub.2 CH.sub.3                                                             CHCH.sub.3 CH.sub.3                                                                       HCH.sub.3                                                                                ##STR58##                                     SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HOCH.sub.3                                                                              SCH.sub.3                                      SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                CH.sub.3 CH.sub.3                                                                       CH.sub.3                                       SO.sub.2 SO.sub.2 CH.sub.3                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                CH.sub. 3 CH.sub.3                                                                      OCH.sub.3                                      SOSOH    HHH         HCH.sub.3 CH.sub.3                                       SOSOH    HHH         HOCH.sub.3                                                                              OCH.sub.3                                      SOSOH    HHH         HOCH.sub.3                                                                              SCH.sub.3                                      SOSOH    HHH         HCH.sub.3 N(CH.sub.3).sub.2                              SOSOCH.sub.3                                                                           HHH         HCH.sub.3 OCH.sub.3                                      SOSOCH.sub.3                                                                           CH.sub.3 CH.sub.3 CH.sub.3                                                                HCH.sub.3 OCH.sub.3                                      OSH      HHH         HCH.sub.3 OCH.sub.3                                      OSCH.sub.3                                                                             CH.sub.3 CH.sub.3 CH.sub.3                                                                HCH.sub.3 CH.sub.3                                       OSOH     HHH         HCH.sub.3 OCH.sub.3                                      OSO.sub.2 H                                                                            HHH         HCH.sub.3 OCH.sub.3                                      OSO.sub.2 CH.sub.3                                                                     HCH.sub.3 H HCH.sub.3 OCH.sub.3                                      SOH      HHH         HCH.sub.3 OCH.sub.3                                      SOOH     HHH         HCH.sub.3 OCH.sub.3                                      SO.sub.2 OH                                                                            HHH         HCH.sub.3 OCH.sub.3                                      SO.sub.2 SH                                                                            HHH         HCH.sub.3 OCH.sub.3                                      SO.sub.2 SH                                                                            HHH         HCH.sub.3 OCH.sub.3                                      S SOH    HHH         HCH.sub.3 OCH.sub.3                                      SSO.sub.2 H                                                                            HHH         HCH.sub.3 OCH.sub.3                                      SSO.sub.2 CH.sub.3                                                                     HCH.sub.3 H HCH.sub.3 OCH.sub.3                                      SO.sub.2 SOH                                                                           HHH         HCH.sub.3 OCH.sub.3                                      SOSO.sub.2 H                                                                           HHH         HCH.sub.3 OCH.sub.3                                      ______________________________________                                    

                  TABLE IIb                                                       ______________________________________                                         ##STR59##                                                                                                                      m.p.                        W.sub.1                                                                            W      R.sub.3                                                                              R.sub.4                                                                            R.sub.5                                                                            R.sub.6                                                                            R.sub.7                                                                            X     Y    (°C.)                ______________________________________                                        O    O      H      H    H    H    H    CH.sub.3                                                                            CH.sub.3                         O    O      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        O    O      H      H    H    H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 O    O      H      H    H    H    H    CH.sub.3                                                                            N(CH.sub.3).sub.2                O    O      H      H    H    H    H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3               O    O      H      H    H    H    H    CH.sub.3                                                                            SCH.sub.3                        O    O      H      H    H    H    H    OCH.sub.3                                                                           SCH.sub.3                        O    O      H      H    H    H    H    OCH.sub.3                                                                           OCH.sub.3                        O    O      H      H    H    H    H    OCH.sub.3                                                                           OC.sub.2 H.sub.5                 O    O      H      H    H    H    H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3               O    O      H      H    H    H    H    OCH.sub.3                                                                           NH.sub.2                         O    O      H      H    H    H    H    OCH.sub.3                                                                           NHCH.sub.3                       O    O      H      H    H    H    H    OCH.sub.3                                                                           N(CH.sub.3).sub.2                O    O      H      H    H    H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                        O    O      H      H    H    H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                        O    O      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            CH.sub.3                         O    O      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        O    O      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            CH(OCH.sub.3).sub.2              O    O      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3               O    O      CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           OCH.sub.3                        O    O      CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                            ##STR60##                       O    O      CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3               O    O      CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           SCH.sub.3                        O    O      CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    CH.sub.3                                                                            OCH.sub.3                        O    O      CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 O    O      CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    OCH.sub.3                                                                           H                                O    O      CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    CH.sub.3                                                                            CH.sub.3                         O    O      CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    CH.sub.3                                                                            OCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    OCH.sub.3                                                                           OCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    CH.sub.3                                                                            CH.sub.3                         O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    CH.sub.3                                                                            OCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub. 3                                                                           N(CH.sub.3).sub.2                O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                                                                             ##STR61##                       O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           SCH.sub.3                        O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           N(CH.sub.3).sub.2                O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                         O    O      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                        S    S      H      H    H    H    H    CH.sub.3                                                                            CH.sub.3                         S    S      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        S    S      H      H    H    H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 S    S      H      H    H    H    H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3               S    S      H      H    H    H    H    OCH.sub.3                                                                           H                                S    S      H      H    H    H    H    OCH.sub.3                                                                           OCH.sub.3                        S    S      H      H    H    H    H    OCH.sub.3                                                                           OC.sub.2 H.sub.5                 S    S      H      H    H    H    H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3               S    S      H      H    H    H    H    OCH.sub.3                                                                           SCH.sub.3                        S    S      H      H    H    H    CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                         S    S      H      H    H    H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                        S    S      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            CH.sub.3                         S    S      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        S    S      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 S    S      CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3               S    S      CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           OCH.sub.3                        S    S      CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           OC.sub.2 H.sub.5                 S    S      CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3               S    S      CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 S    S      CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    OCH.sub.3                                                                           H                                S    S      CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    CH.sub.3                                                                            CH.sub.3                         S    S      CH.sub.3                                                                             CH.sub. 3                                                                          H    H    H    CH.sub.3                                                                            OCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    OCH.sub.3                                                                           OCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    CH.sub.3                                                                            CH.sub.3                         S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    CH.sub.3                                                                            OCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                                                                            NH.sub.2                         S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                                                                            NHCH.sub.3                       S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                                                                            N(CH.sub.3).sub.2                S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           SCH.sub.3                        S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                         S    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3               SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            N(CH.sub.3).sub.2                SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    OCH.sub.3                                                                           OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    OCH.sub.3                                                                           OC.sub.2 H.sub.5                 SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3               SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             H      H    H    H    CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            CH.sub.2 OCH.sub.3               SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    H    H    H    OCH.sub. 3                                                                          OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           OC.sub.2 H.sub.5                 SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    H    H    H    OCH.sub.3                                                                           CH.sub.2 OCH.sub.3               SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    CH.sub.3                                                                            OC.sub.2 H.sub.5                 SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    OCH.sub.3                                                                           H                                SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    CH.sub.3                                                                            CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           H    H    H    OCH.sub.3                                                                           OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    CH.sub.3                                                                            CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           H    H    OCH.sub.3                                                                           OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub. 3                                                                          H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           NHCH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                             CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           OCH.sub.3                                                                           OCH.sub.3                        SO   SO     H      H    H    H    H    CH.sub.3                                                                            CH.sub.3                         SO   SO     H      H    H    H    H    CH.sub.3                                                                            SCH.sub.3                        SO   SO     H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO   SO     H      H    H    H    H    OCH.sub.3                                                                           OCH.sub.3                        SO   SO     CH.sub.3                                                                             H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO   SO     CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    CH.sub.3                                                                            OCH.sub.3                        O    S      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        O    S      CH.sub.3                                                                             CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                                                                           H    OCH.sub.3                                                                           SCH.sub.3                        O    SO     H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        O    SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        O    SO.sub.2                                                                             CH.sub. 3                                                                            H    CH.sub.3                                                                           H    H    CH.sub.3                                                                            OCH.sub.3                        S    O      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO   O      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           O      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO   S      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           S      H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        S    SO     H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        S    SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        S    SO.sub.2                                                                             CH.sub.3                                                                             H    CH.sub.3                                                                           H    H    CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO     H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        SO   SO.sub.2                                                                             H      H    H    H    H    CH.sub.3                                                                            OCH.sub.3                        ______________________________________                                    

                  TABLE IIc                                                       ______________________________________                                         ##STR62##                                                                    W.sub.1                                                                            W       R.sub.3                                                                              R.sub.4                                                                             R.sub.5                                                                            R.sub.6                                                                             R.sub.7                                                                            G    X.sub.1                        ______________________________________                                        O    O       H      H     H    H     H    CH.sub.2                                                                           CH.sub.3                       O    O       H      H     H    H     H    CH.sub.2                                                                           OCH.sub.3                      O    O       H      H     H    H     H    O    CH.sub.3                       O    O       H      H     H    H     H    O    OCH.sub.3                      O    O       H      H     H    H     CH.sub.3                                                                           CH.sub.3                                                                           CH.sub.3                       O    O       H      H     H    H     CH.sub.3                                                                           O    OCH.sub.3                      O    O       CH.sub.3                                                                             H     H    H     H    O    CH.sub.3                       O    O       CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    CH.sub.2                                                                           OCH.sub.3                      O    O       CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    O    CH.sub.3                       O    O       CH.sub.3                                                                             H     CH.sub.3                                                                           H     O    O    OCH.sub.3                      O    O       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           H     H    O    OCH.sub.3                      O    O       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    CH.sub.2                                                                           CH.sub.3                       O    O       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    CH.sub.3                       O    O       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    OCH.sub.3                      O    O       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.2                                                                           CH.sub.3                       O    O       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                           O    OCH.sub.3                      S    S       H      H     H    H     H    CH.sub.2                                                                           CH.sub.3                       S    S       H      H     H    H     H    CH.sub.2                                                                           OCH.sub.3                      S    S       H      H     H    H     H    O    CH.sub.3                       S    S       H      H     H    H     H    O    OCH.sub.3                      S    S       H      H     H    H     CH.sub.3                                                                           CH.sub.2                                                                           CH.sub.3                       S    S       H      H     H    H     CH.sub.3                                                                           O    OCH.sub.3                      S    S       CH.sub.3                                                                             H     H    H     H    O    CH.sub.3                       S    S       CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    CH.sub.2                                                                           OCH.sub.3                      S    S       CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    O    CH.sub.3                       S    S       CH.sub.3                                                                             H     CH.sub.3                                                                           H     O    O    OCH.sub.3                      S    S       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           H     H    O    OCH.sub.3                      S    S       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    CH.sub.2                                                                           CH.sub.3                       S    S       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    CH.sub.3                       S    S       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    OCH.sub.3                      S    S       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.2                                                                           CH.sub.3                       S    S       CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                           O    CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              H      H     H    H     H    CH.sub.2                                                                           CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              H      H     H    H     H    CH.sub.2                                                                           OCH.sub.3                      SO.sub.2                                                                           SO.sub.2                                                                              H      H     H    H     H    O    CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              H      H     H    H     H    O    OCH.sub.3                      SO.sub.2                                                                           SO.sub.2                                                                              H      H     H    H     CH.sub.3                                                                           CH.sub.2                                                                           CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              H      H     H    H     CH.sub. 3                                                                          O    CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              H      H     H    H     CH.sub.3                                                                           O    OCH.sub.3                      SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             H     H    H     H    O    CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    CH.sub.2                                                                           OCH.sub.3                      SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    O    CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             H     CH.sub.3                                                                           H     O    O    OCH.sub.3                      SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           H     H    O    OCH.sub.3                      SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    CH.sub.2                                                                           CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    OCH.sub.3                      SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.2                                                                           CH.sub.3                       SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            CH.sub.3                                                                           O    OCH.sub.3                      SO   SO      H      H     H    H     H    CH.sub.2                                                                           CH.sub.3                       SO   SO      H      H     H    H     H    O    OCH.sub.3                      SO   SO      H      H     H    H     H    O    CH.sub.3                       SO   SO      CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    O    CH.sub.3                       SO   SO      CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    CH.sub.3                       O    S       H      H     H    H     H    O    CH.sub.3                       O    SO      H      H     H    H     H    O    CH.sub.3                       O    SO.sub.2                                                                              H      H     H    H     H    O    CH.sub.3                       O    SO.sub.2                                                                              CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    O    CH.sub.3                       O    SO.sub.2                                                                              CH.sub.3                                                                             CH.sub.3                                                                            CH.sub.3                                                                           CH.sub.3                                                                            H    O    CH.sub.3                       S    O       H      H     H    H     H    O    CH.sub.3                       SO   O       H      H     H    H     H    O    CH.sub.3                       SO.sub.2                                                                           O       H      H     H    H     H    O    CH.sub.3                       SO   S       H      H     H    H     H    O    CH.sub.3                       SO.sub.2                                                                           S       H      H     H    H     H    O    CH.sub.3                       S    SO      H      H     H    H     H    O    CH.sub.3                       S    SO.sub.2                                                                              H      H     H    H     H    O    CH.sub.3                       S    SO.sub.2                                                                              CH.sub.3                                                                             H     CH.sub.3                                                                           H     H    O    CH.sub.3                       SO.sub.2                                                                           SO      H      H     H    H     H    O    CH.sub.3                       SO   SO.sub.2                                                                              H      H     H    H     H    O    CH.sub.3                   

                  TABLE IId                                                       ______________________________________                                         ##STR63##                                                                    W.sub.1                                                                            W       R.sub.3 R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                             R.sub.7                                                                             X.sub.1                          ______________________________________                                        O    O       H       H     H     H     H     CH.sub.3                         O    O       H       H     H     H     H     OCH.sub.3                        O    O       H       H     H     H     CH.sub.3                                                                            CH.sub.3                         O    O       H       H     H     H     CH.sub.3                                                                            OCH.sub.3                        O    O       CH.sub.3                                                                              H     H     H     H     CH.sub.3                         O    O       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        O    O       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        O    O       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            H     H     H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            H     H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                        S    S       H       H     H     H     H     CH.sub.3                         S    S       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         S    S       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        S    S       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     CH.sub.3                         S    S       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        S    S       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                         S    S       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                              H       H     H     H     H     CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                              H       H     H     H     H     OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              H     CH.sub. 3                                                                           H     H     CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        SO   SO      H       H     H     H     H     CH.sub.3                         SO   SO      H       H     H     H     H     OCH.sub.3                        SO   SO      CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         SO   SO      CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        O    S       H       H     H     H     H     OCH.sub.3                        O    SO      H       H     H     H     H     OCH.sub.3                        O    SO.sub.2                                                                              H       H     H     H     H     OCH.sub.3                        O    SO.sub.2                                                                              H       CH.sub.3                                                                            H     CH.sub.3                                                                            H     CH.sub.3                         O    SO.sub.2                                                                              H       CH.sub.3                                                                            H     CH.sub.3                                                                            H     OCH.sub.3                        O    SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        S    O       H       H     H     H     H     CH.sub.3                         SO   O       H       H     H     H     H     CH.sub.3                         SO.sub.2                                                                           O       H       H     H     H     H     CH.sub.3                         SO   S       H       H     H     H     H     CH.sub.3                         SO.sub.2                                                                           S       H       H     H     H     H     CH.sub.3                         S    SO      H       H     H     H     H     CH.sub.3                         S    SO.sub.2                                                                              H       H     H     H     H     CH.sub.3                         S    SO.sub.2                                                                              CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         S    SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            H     CH.sub.3                                                                            H     CH.sub.3                         SO.sub.2                                                                           SO      H       H     H     H     H     CH.sub.3                         SO   SO.sub.2                                                                              H       H     H     H     H     CH.sub.3                         ______________________________________                                    

                  TABLE IIe                                                       ______________________________________                                         ##STR64##                                                                    W.sub.1                                                                            W       R.sub.3 R.sub.4                                                                             R.sub.5                                                                             R.sub.6                                                                             R.sub.7                                                                             X.sub.1                          ______________________________________                                        O    O       H       H     H     H     H     CH.sub.3                         O    O       H       H     H     H     H     OCH.sub.3                        O    O       H       H     H     H     CH.sub.3                                                                            CH.sub.3                         O    O       H       H     H     H     CH.sub.3                                                                            OCH.sub.3                        O    O       CH.sub.3                                                                              H     H     H     H     CH.sub.3                         O    O       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        O    O       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            H     H     H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            H     H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                         O    O       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                        S    S       H       H     H     H     H     CH.sub.3                         S    S       H       H     H     H     H     OCH.sub.3                        S    S       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         S    S       CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        S    S       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     CH.sub.3                         S    S       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        S    S       CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                              H       H     H     H     H     CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                              H       H     H     H     H     OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                              H       H     H     H     CH.sub.3                                                                            OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                         SO.sub.2                                                                           SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            OCH.sub.3                        SO   SO      H       H     H     H     H     CH.sub.3                         SO   SO      H       H     H     H     H     OCH.sub.3                        SO   SO      CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         SO   SO      CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     OCH.sub.3                        O    S       H       H     H     H     H     OCH.sub.3                        O    SO      H       H     H     H     H     OCH.sub.3                        O    SO.sub.2                                                                              H       H     H     H     H     OCH.sub.3                        O    SO.sub.2                                                                              H       CH.sub.3                                                                            H     CH.sub.3                                                                            H     CH.sub.3                         O    SO.sub.2                                                                              H       CH.sub.3                                                                            H     CH.sub.3                                                                            H     OCH.sub.3                        O    SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            CH.sub.3                                                                            CH.sub.3                                                                            H     OCH.sub.3                        S    O       H       H     H     H     H     CH.sub.3                         SO   O       H       H     H     H     H     CH.sub.3                         SO.sub.2                                                                           O       H       H     H     H     H     CH.sub.3                         SO   S       H       H     H     H     H     CH.sub.3                         SO.sub.2                                                                           S       H       H     H     H     H     CH.sub.3                         S    SO      H       H     H     H     H     CH.sub.3                         S    SO.sub.2                                                                              H       H     H     H     H     CH.sub.3                         S    SO.sub.2                                                                              CH.sub.3                                                                              H     CH.sub.3                                                                            H     H     CH.sub.3                         S    SO.sub.2                                                                              CH.sub.3                                                                              CH.sub.3                                                                            H     CH.sub.3                                                                            H     CH.sub.3                         SO.sub.2                                                                           SO      H       H     H     H     H     CH.sub.3                         SO   SO.sub.2                                                                              H       H     H     H     H     CH.sub.3                         ______________________________________                                    

                  TABLE IIf                                                       ______________________________________                                         ##STR65##                                                                    W.sub.1 W                                                                            R.sub.3 R.sub.4                                                                        R.sub.5 R.sub.6                                                                        R.sub.7                                                                            X.sub.2  Y.sub.2                                ______________________________________                                        OO     HH       HH       H    CH.sub.3 OCH.sub.3                              OO     HH       HH       H    CH.sub.2 CF.sub.3                                                                      SCH.sub.3                              OO     HH       HH       H    CH.sub.2 CF.sub.3                                                                      OCH.sub.2 CH.sub.3                     OO     HH       HH       CH.sub.3                                                                           CH.sub.3 OCH.sub.3                              OO     HH       HH       CH.sub.3                                                                           CH.sub.3 SCH.sub.3                              OO     CH.sub.3 H                                                                             HH       H    C.sub.2 H.sub.5                                                                        OCH.sub.3                              OO     CH.sub.3 H                                                                             CH.sub.3 H                                                                             H    CH.sub.3 OC.sub.2 H.sub.5                       OO     CH.sub.3 H                                                                             CH.sub.3 H                                                                             H    CH.sub.2 CF.sub.3                                                                      SCH.sub.3                              OO     CH.sub.3 CH.sub.3                                                                      CH.sub.3 H                                                                             H    CH.sub.3 CH.sub.2 CH.sub.2                                                             OCH.sub.3                              OO     CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    CH.sub.3 OCH.sub.3                              OO     CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    CH.sub.3 SCH.sub.3                              OO     CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    CH.sub.3 CH.sub.2 CH.sub.2                                                             SCH.sub.3                              OO     CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    (CH.sub.3).sub.2 CH                                                                    SC.sub.2 H.sub.5                       OO     CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      CH.sub.3                                                                           CH.sub.3 OCH.sub.3                              SS     HH       HH       H    CH.sub.3 OCH.sub.3                              SS     HH       HH       H    CH.sub.3 SCH.sub.3                              SS     HH       HH       CH.sub.3                                                                           CH.sub.3 OCH.sub.3                              SS     CH.sub.3 H                                                                             HH       H    CH.sub.3 OCH.sub.3                              SS     CH.sub.3 H                                                                             CH.sub.3 H                                                                             H    CH.sub.3 OCH.sub.3                              SS     CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    CH.sub.3 OCH.sub.3                              SO.sub.2 SO.sub.2                                                                    HH       HH       H    CH.sub.3 OCH.sub.3                              SO.sub.2 SO.sub.2                                                                    HH       HH       H    CH.sub.3 SCH.sub.3                              SO.sub.2 SO.sub.2                                                                    HH       HH       H    CH.sub.2 CF.sub.3                                                                      OCH.sub.3                              SO.sub.2 SO.sub.2                                                                    HH       HH       CH.sub.3                                                                           CH.sub.3 OCH.sub.3                              SO.sub.2 SO.sub.2                                                                    CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    CH.sub.3 OCH.sub.3                              SO.sub.2 SO.sub.2                                                                    CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      CH.sub.3                                                                           CH.sub.3 OCH.sub.3                              SOSO   HH       HH       H    CH.sub.3 OCH.sub.3                              SOSO   CH.sub.3 H                                                                             CH.sub.3 H                                                                             H    CH.sub.3 OCH.sub.3                              SOSO   CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    CH.sub.3 OCH.sub.3                              OS     HH       HH       H    CH.sub.3 OCH.sub.3                              OSO    HH       HH       H    CH.sub.3 OCH.sub.3                              OSO.sub.2                                                                            HH       HH       H    CH.sub.3 OCH.sub.3                              OSO.sub.2                                                                            CH.sub.3 H                                                                             CH.sub.3 H                                                                             H    CH.sub.3 OCH.sub.3                              OSO.sub.2                                                                            CH.sub.3 CH.sub.3                                                                      CH.sub.3 CH.sub.3                                                                      H    CH.sub.3 OCH.sub.3                              SO     HH       HH       H    CH.sub.3 OCH.sub.3                              SOO    HH       HH       H    CH.sub.3 OCH.sub.3                              SO.sub.2 O                                                                           HH       HH       H    CH.sub.3 OCH.sub.3                              SOS    HH       HH       H    CH.sub.3 OCH.sub.3                              SO.sub.2 S                                                                           HH       HH       H    CH.sub.3 OCH.sub.3                              SSO    HH       HH       H    CH.sub.3 OCH.sub.3                              SSO.sub.2                                                                            HH       HH       H    CH.sub.3 OCH.sub.3                              SO.sub.2 SO                                                                          HH       HH       H    CH.sub.3 OCH.sub.3                              SOSO.sub.2                                                                           HH       HH       H    CH.sub.3 OCH.sub.3                              ______________________________________                                    

Formulations

Useful formulations of the compounds of Formulae I and II can beprepared in conventional ways. They include dusts, granules, pellets,solutions, suspensions, emulsions, wettable powders, emulsifiableconcentrates and the like. Many of these may be applied directly.Sprayable formulations can be extended in suitable media and used atspray volumes of from a few liters to several hundred liters perhectare. High strength compositions are primarily used as intermediatesfor further formulation. The formulations, broadly, contain about 0.1%to 99% by weight of active ingredient(s) and at least one (a) about 0.1%to 20% surfactant(s) and (b) about 1% to 99.9% solid or liquid inertdiluent(s). More specifically, they will contain these ingredients inthe following approximate proportions:

                  TABLE 12                                                        ______________________________________                                                    Active  Weight Percent*                                                       Ingredient                                                                            Diluent(s)                                                                              Surfactant(s)                                   ______________________________________                                        Wettable Powders                                                                            20-90      0-74     1-10                                        Oil Suspensions,                                                                             3-50     40-95     0-15                                        Emulsions, Solutions,                                                         (including Emulsifiable                                                       Concentrates)                                                                 Aqueous Suspension                                                                          10-50     40-84     1-20                                        Dusts          1-25     70-99     0-5                                         Granules and Pellets                                                                        0.1-95      5-99.9  0-15                                        High Strength 90-99      0-10     0-2                                         Compositions                                                                  ______________________________________                                         *Active ingredient plus at least one of a Surfactant or a Diluent equals      100 weight percent.                                                      

Lower or higher levels of active ingredient can, of course, be presentdepending on the intended use and the physical properties of thecompound. Higher ratios of surfactant to active ingredient are sometimesdesirable, and are achieved by incorporation into the formulation or bytank mixing.

Typical solid diluents are described in Watkins, et al., "Handbook ofInsecticide Dust Diluents and Carriers", 2nd Ed., Dorland Books,Caldwell, N.J., but other solids, either mined or manufactured, may beused. The more absorptive diluents are preferred for wettable powdersand the denser ones for dusts. Typical liquid diluents and solvents aredescribed in Marsden, "Solvents Guide," 2nd Ed., Interscience, New York,1950. Solubility under 0.1% is preferred for suspension concentrates;solution concentrates are preferably stable against phase separation at0° C. "McCutcheon's Detergents and Emulsifiers Annual", MC PublishingCorp., Ridgewood, N.J., as well as Sisely and Wood, "Encyclopedia ofSurface Active Agents", Chemical Publishing Co., Inc., New York, 1964,list surfactants and recommended uses. All formulations can containminor amounts of additives to reduce foaming, caking, corrosion,microbiological growth, etc.

The methods of making such compositions are well known. Solutions areprepared by simply mixing the ingredients. Fine solid compositions aremade by blending and, usually, grinding as in a hammer or fluid energymill. Suspensions are prepared by wet milling (see, for example,Littler, U.S. Pat. No. 3,060,084). Granules and pellets may be made byspraying the active material upon preformed granular carriers or byagglomeration techniques. See J. E. Browning, "Agglomeration", ChemicalEngineering, Dec. 4, 1967, pp. 147ff. and "Perry's Chemical Engineer'sHandbook", 5th Ed., McGraw-Hill, New York, 1973, pp. 8-57ff.

For further information regarding the art of formulation, see forexample:

H. M. Loux, U.S. Pat. No. 3,235,361, Feb. 15, 1966, Col. 6, line 16through Col. 7, line 19 and Examples 10 through 41;

R. W. Luckenbaugh, U.S. Pat. No. 3,309,192, Mar. 14, 1967, Col. 5, line43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58,132, 138-140, 162-164, 166, 167 and 169-182;

H. Gysin and E. Knusli, U.S. Pat. No. 2,891,855, June 23, 1959, Col. 3,line 66 through Col. 5, line 17 and Examples 1-4;

G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc.,New York, 1961, pp. 81-96; and

J. D. Fryer and S. A. Evans, "Weed Control Handbook", 5th Ed., BlackwellScientific Publications, Oxford, 1968, pp. 101-103.

In the following examples, all parts are by weight unless otherwiseindicated.

EXAMPLE 21 Wettable Powder

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:80%

sodium alkylnaphthalenesulfonate: 2%

sodium ligninsulfonate: 2%

synthetic amorphous silica: 3%

kaolinite: 13%

The ingredients are blended, hammer-milled until all the solids areessentially under 50 microns, reblended, and packaged.

EXAMPLE 22 Wettable Powder

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:50%

sodium alkylnaphthalenesulfonate: 2%

low viscosity methyl cellulose: 2%

diatomaceous earth: 46%

The ingredients are blended, coarsely hammer-milled and then air-milledto produce particles essentially all below 10 microns in diameter. Theproduct is reblended before packaging.

EXAMPLE 23 Granule

Wettable Power of Example 22: 5%

attapulgite granules (U.S.S. 20-40 mesh; 0.84-0.42 mm): 95%

A slurry of wettable powder containing ≈25% solids is sprayed on thesurface of attapulgite granules in a double-cone blender. The granulesare dried and packaged.

EXAMPLE 24 Extruded Pellet

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:25%

anhydrous sodium sulfate: 10%

crude calcium ligninsulfonate: 5%

sodium alkylnaphthalenesulfonate: 1%

calcium/magnesium bentonite: 59%

The ingredients are blended, hammer-milled and then moistened with about12% water. The mixture is extruded as cylinders about 3 mm diameterwhich are cut to produce pellets about 3 mm long. These may be useddirectly after drying, or the dried pellets may be crushed to pass aU.S.S. No. 20 sieve (0.84 mm openings). The granules held on a U.S.S.No. 40 sieve (0.42 mm openings) may be packaged for use and the finesrecycled.

EXAMPLE 25 Oil Suspension

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:25%

polyoxyethylene sorbitol hexaoleate: 5%

highly aliphatic hydrocarbon oil: 70%

The ingredients are ground together in a sand mill until the solidparticles have been reduced to under about 5 microns. The resultingthick suspension may be applied directly, but preferably after beingextended with oils or emulsified in water.

EXAMPLE 26 Wettable Powder

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:20%

sodium alkylnaphthalenesulfonate: 4%

sodium ligninsulfonate: 4%

low viscosity methyl cellulose: 3%

attapulgite: 69%

The ingredients are thoroughly blended. After grinding in a hammer-millto produce particles essentially all below 100 microns, the material isreblended and sifted through a U.S.S. No. 50 sieve (0.3 mm opening) andpackaged.

EXAMPLE 27 Low Strength Granule

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-1,4-benzodioxan-4-sulfonamide:1%

N,N-dimethylformamide: 9%

attapulgite granules (U.S.S. 20-40 sieve): 90%

The active ingredient is dissolved in the solvent and the solution issprayed upon dedusted granules in a double cone blender. After sprayingof the solution has been completed, the blender is allowed to run for ashort period and then the granules are packaged.

EXAMPLE 28 Aqueous Suspension

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:40%

polyacrylic acid thickener: 0.3%

dodecylphenol polyethylene glycol ether: 0.5%

disodium phosphate: 1%

monosodium phosphate: 0.5%

polyvinyl alcohol: 1.0%

water: 56.7%

The ingredients are blended and ground together in a sand mill toproduce particles essentially all under 5 microns in size.

EXAMPLE 29 Solution

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide,sodium salt: 5%

water: 95%

The salt is added directly to the water with stirring to produce thesolution, which may then be packaged for use.

EXAMPLE 30 Low Strength Granule

N-[(4,6-dimethyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:0.1%

attapulgite granules (U.S.S. 20-40 mesh): 99.9%

The active ingredient is dissolved in a solvent and the solution issprayed upon dedusted granules in a double-cone blender. After sprayingof the solution has been completed, the material is warmed to evaporatethe solvent. The material is allowed to cool and then packaged.

EXAMPLE 31 Granule

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:80%

wetting agent: 1%

crude ligninsulfonate salt (containing 5-20% of the natural sugars): 10%

attapulgite clay: 9%

The ingredients are blended and milled to pass through a 100 meshscreen. This material is then added to a fluid bed granulator, the airflow is adjusted to gently fluidize the material, and a fine spray ofwater is sprayed onto the fluidized material. The fluidization andspraying are continued until granules of the desired size range aremade. The spraying is stopped, but fluidization is continued, optionallywith heat, until the water content is reduced to the desired level,generally less than 1%. The material is then discharged, screened to thedesired size range, generally 14-100 mesh (1410-149 microns), andpackaged for use.

EXAMPLE 32 High Strength Concentrate

N-[(4,6-dimethoxy-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:99%

silica aerogel: 0.5%

synthetic amorphous silica: 0.5%

The ingredients are blended and ground in a hammer-mill to produce amaterial essentially all passing a U.S.S. No. 50 screen (0.3 mmopening). The concentrate may be formulated further if necessary.

EXAMPLE 33 Wettable Powder

N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:90%

dioctyl sodium sulfosuccinate: 0.1%

synthetic fine silica: 9.9%

The ingredients are blended and ground in a hammer-mill to produceparticles essentially all below 100 microns. The material is siftedthrough a U.S.S. No. 50 screen and then packaged.

EXAMPLE 34 Wettable Powder

N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4sulfonamide:40%

sodium ligninsulfonate: 20%

montmorillonite clay: 40%

The ingredients are thoroughly blended, coarsely hammer-milled and thenair-milled to produce particles essentially all below 10 microns insize. The material is reblended and then packaged.

EXAMPLE 35 Oil Suspension

N-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:35%

blend of polyalcohol carboxylic esters and oil soluble petroleumsulfonates: 6%

xylene: 59%

The ingredients are combined and ground together in a sand mill toproduce particles essentially all below 5 microns. The product can beused directly, extended with oils, or emulsified in water.

EXAMPLE 36 Dust

N-[(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide:10%

attapulgite: 10%

Pyrophyllite: 80%

The active ingredient is blended with attapulgite and then passedthrough a hammer-mill to produce particles substantially all below 200microns. The ground concentrate is then blended with powderedpyrophyllite until homogeneous.

Utility

The compounds of the present invention are powerful herbicides. Theyhave utility for broad-spectrum pre- and/or post-emergence weed controlin areas where complete control of all vegetation is desired, such asaround fuel storage tanks, ammunition depots, industrial storage areas,parking lots, drive-in theaters, around billboards, highway and railroadstructures. Alternatively, the subject compounds are useful forselective pre- or post-emergence weed control in crops, such as wheat,barley and rice.

The rates of application for the compounds of the invention aredetermined by a number of factors, including their use as selective orgeneral herbicides, the crop species involved, the types of weeds to becontrolled, weather and climate, formulations selected, mode ofapplication, amount of foliage present, etc. In general terms, thesubject compounds should be applied at levels of around 0.125 to 10kg/ha, the lower rates being suggested for use on lighter soils and/orthose having a low organic matter content, for selective weed control orfor situations where only short-term persistence is required.

The compounds of the invention may be used in combination with any othercommercial herbicide examples of which are those of the triazine,triazole, uracil, urea, amide, diphenylether, carbamate and bipyridyliumtypes.

The herbicidal properties of the subject compounds were discovered in anumber of greenhouse tests. The test procedures and results follow.

Test A

Seeds of crabgrass (Digitaria sp.), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), sicklepod (Cassia obtusifolia),morningglory (Ipomoea sp.), cocklebur (Xanthium sp.), sorghum, corn,soybean, rice, wheat and nutsedge tubers (Cyperus rotundus) were plantedin a growth medium and treated pre-emergence with a non-phytotoxicsolvent solution of the compounds of Table A. At the same time, cottonhaving five leaves, bush beans with the third trifoliate leaf expanding,crabgrass and barnyardgrass with two leaves, wild oats with two leaves,sicklepod with three leaves, morningglory and cocklebur with fourleaves, sorghum with four leaves, corn with four leaves, soybean withtwo leaves, rice with three leaves, wheat with one leaf, and nutsedgewith three to five leaves were sprayed with a non-phytotoxic solventsolution of the compounds of Table A. Other containers of the abovementioned weeds and crops were treated pre- or post-emergence with thesame non-phytotoxic solvent so as to provide a solvent control. A set ofuntreated control plants was also included for comparison. Pre-emergenceand post-emergence treated plants and controls were maintained in agreenhouse for sixteen days, then all treated plants were compared withtheir respective controls and rated visually for response to treatment.

The following rating system was used:

0=no effect;

10=maximum effect;

C=chlorosis or necrosis;

D=defoliation;

E=emergence inhibition;

G=growth retardation;

H=formative effects;

U=unusual pigmentation;

I=increased chlorophyl; and

6Y=abscised buds or flowers.

Considering the low rates of application, the data clearly demonstratethe high herbicidal activity of the compounds tested. ##STR66##

                                      TABLE A                                     __________________________________________________________________________            Cmpd. 1                                                                            Cmpd. 1                                                                             Cmpd. 2                                                                             Cmpd. 2                                                                             Cmpd. 3                                                                             Cmpd. 3                                                                            Cmpd. 4                                                                             Cmpd. 5                                                                            Cmpd. 6                  Rate kg/ha                                                                            0.4  0.1   0.05  0.4   0.05  0.4  0.05  0.05 .05                      __________________________________________________________________________    POST-EMERGENCE                                                                Bush bean                                                                             9C   8D,9G,6Y                                                                            3C,9G,6Y                                                                            5C,9G,6Y                                                                            7C,9G,6Y                                                                            9C   5C,9G,6Y                                                                            9C   0                        Cotton  9C   6C,9G 3C,3H,8G                                                                            4C,9G 4C,3H,9G                                                                            6C,9G                                                                              4C,8G 5C,9G                                                                              0                        Morningglory                                                                          10C  9C    2C,4G 6C,9G 5G    5G   10C   10C  2C,2H                    Cocklebur                                                                             9C   9C    2C,6G 5C,9G 5C,9G 9C   10C   9C   1C                       Sicklepod                                                                             9C   6C,9G 4C    4C,6H 5C,9G 9C   4C,9G 9C   0                        Nutsedge                                                                              4C,9G                                                                              9G,5X 4G    2C,9G 2C,9G 3C,9G                                                                              6G    0    0                        Crabgrass                                                                             1C,9G                                                                              2H,8G 0     4G    4G    5G   2C,8G 6G   0                        Barnyardgrass                                                                         9C   5C,9H 2C,8H 9H    3C,9H 9C   4C,9H 9H   0                        Wild Oats                                                                             3C,9G                                                                              2C,9G 2G    2C,5G 1C,6G 2C,9G                                                                              9G    2C,9G                                                                              0                        Wheat   3C,9G                                                                              0     0     0     3G    1C,8G                                                                              9G    2G   0                        Corn    5U,9C                                                                              3U,9G 2C,8H 2C,9H 3C,9H 1C,9H                                                                              5U,9C 3C,9G                                                                              0                        Soybean 9C   9C    2C,5G 3C,8G 5C,8H 9C   9C    9C   0                        Rice    9C   3C,9G 0     5G    1G    1C,6G                                                                              6C,9G 2C,8G                                                                              0                        Sorghum 4U,9G                                                                              9G    2C,8H 2C,9H 2C,9G 2C,9G                                                                              5C,9G 5C,9G                                                                              0                        Sugar beet                                           2C,7G                    PRE-EMERGENCE                                                                 Morningglory                                                                          9H   2C,9H 5G    9G    2G    7G   10C   8H   0                        Cocklebur                                                                             9H   9H    5H    --    8H    9H   9H    9H   0                        Sicklepod                                                                             9C   9G    4H    7G    8G    9G   2C,9G 2C,9G                                                                              0                        Nutsedge                                                                              9G   8G    0     9G    10E   10E  0     5G   0                        Crabgrass                                                                             3C,8G                                                                              1C,6G 0     0     0     2C,4G                                                                              2C    3G   0                        Barnyardgrass                                                                         5C,9H                                                                              9H    2C,4G 2C,8H 3C,9H 9H   3C,9H 2C,8H                                                                              0                        Wild Oats                                                                             3C,9H                                                                              2C,9G 1C,3G 2C,7G 2C,6G 3C,8H                                                                              3C,9G 2C,6G                                                                              0                        Wheat   2C,9G                                                                              2C,9G 0     7G    2C,5G 2C,8G                                                                              1C,9G 1C,6G                                                                              0                        Corn    10E  5C,9H 2C,6G 2C,9H 2C,9G 5C,9H                                                                              5C,9H 8G   0                        Soybean 9H   8H    1C,1H 2C    7H    9H   9H    3C,5H                                                                              0                        Rice    4C,9H                                                                              3C,8H 2C,3G 2G    2G    6G   5C,7H 0    0                        Sorghum 10E  9H    1C    2C,7H 10H   6C,9H                                                                              10H   4C,9H                                                                              0                        Sugar beet                                           0                        __________________________________________________________________________

It is noted that Compound 6 has demonstrated low activity at a rate of0.05 kg/ha. It is thought that at higher rates, activity would beimproved.

Test B

Two plastic bulb pans were filled with fertilized and limed Fallsingtonsilt loam soil. One pan was planted with corn, sorghum, Kentuckybluegrass and several grassy weeds. The other pan was planted withcotton, soybeans, purple nutsedge (Cyperus rotundus), and severalbroadleaf weeds. The following grassy and broadleaf weeds were planted:crabgrass (Digitaria sanguinalis), barnyardgrass (Echinochloacrusgalli), wild oats (Avena fatua), johnsongrass (Sorghum halepense),dallisgrass (Paspalum dilatatum), giant foxtail (Setaria faberii),cheatgrass (Bromus secalinus), mustard (Brassica arvensis), cocklebur(Xanthium pensylvanicum), pigweed (Amaranthus retroflexus), morningglory(Ipomoea hederacea), sicklepod (Cassia obtusifolia), teaweed (Sidaspinosa), velvetleaf (Abutilion theophrasti), and jimsonweed (Daturastramonium). A 12.5 cm diameter plastic pot was also filled withprepared soil and planted with rice and wheat. Another 12.5 cm pot wasplanted with sugar beets. The above four containers were treatedpre-emergence with several test compounds within the scope of theinvention.

Twenty-eight days after treatment, the plants were evaluated andvisually rated for response to the chemical treatments utilizing therating system described previously for Test A. The data are summarizedin Table B.

                                      TABLE B                                     __________________________________________________________________________    PRE-EMERGENCE ON FALLSINGTON SILT LOAM                                                Compound 1                                                                            Compound 2                                                                              Compound 3      Compound 4                                                                            Compound 5                  Rate kg/ha                                                                            .030                                                                              .120                                                                              .030                                                                             0.060                                                                            .250                                                                              .030                                                                              .120                                                                              0.060                                                                             0.250                                                                             0.060                                                                             0.250                                                                             0.030                                                                             0.120                   __________________________________________________________________________    Crabgrass                                                                             0   0   0  0  0   0   2G  2G  2G  2G  2G  2G  5G                      Barnyardgrass                                                                         6G,3H                                                                             9G,5H                                                                             2G 4G 5G  3G  7G  5G  6G,5H                                                                             6G  8G  6G  8G                      Sorghum 6G,3H                                                                             9G,5H                                                                             3G 3G 6G  8G  8G,8C                                                                             10C 10C 9G  10C 9G  10C                     Wild Oats                                                                             3G  6G,2C                                                                             0  2G 4G  0   4G  3G  5G  4G  6G  6G  8G                      Johnsongrass                                                                          2H  8G,5H                                                                             2G 2G 5G,3H                                                                             5G  8G  7G,5H                                                                             8G,3C                                                                             6G  6G  8G  9G                      Dallisgrass                                                                           0   3G  0  2G 2G  2G  4G  4G  7G  0   3G  2G  8G                      Giant foxtail                                                                         0   0   0  0  0   0   4G  5G  6G,2C                                                                             0   2G  5G  9G                      Ky. bluegrass                                                                         0   4G  0  4G 5G  3G  9G  7G  8G  4G  8G  5G  8G                      Cheatgrass                                                                            3G  6G,6C                                                                             0  2G 4G  9G  9G,9C                                                                             9G,9C                                                                             10C 6G  10C 7G  9G                      Sugar beets                                                                           6G  7G,5C                                                                             2G 2G 5G  3G  8G  9G  9G  9G  9G  9G  10C                     Corn    3G  7G,5H                                                                             0  0  7G,5H                                                                             5G,5H                                                                             10C 8G,7H                                                                             8G,8H                                                                             9G,9C                                                                             10C 9G  10C                     Mustard 9G,9C                                                                             9G,9C                                                                             5G 8G 9G,9C                                                                             8G  8G,8C                                                                             10C 10C 9G,9C                                                                             10C 10C 10C                     Cocklebur                                                                             6G,3H                                                                             7G,5H                                                                             0  0  7G,3H                                                                             5G,3C                                                                             7G,5C                                                                             6G,5H                                                                             7G,5H                                                                             8G,7H                                                                             8G,7H                                                                             8G  9G                      Pigweed 0   5G  -- -- --  --  --  --  --  --  --  --  --                      Nutsedge                                                                              5G  7G  0  0  4G  10C 10C 10C 10C 5G  5G  2G  6G                      Cotton  3G  8G,5H                                                                             2G 6G 6G  0   3G  0   3G,3H                                                                             8G  9G  7G  9G                      Morningglory                                                                          3G  5G,3C                                                                             0  0  3G  3G  3G  0   2G  7G  8G  7G  8G                      Sicklepod                                                                             0   4G,3C                                                                             0  0  0   3G  7G  2G  5G  3G  6G  0   6G                      Teaweed 2C  5G,5H                                                                             0  0  7G  6G  8G  5G  6G  2G  2G  5G  8G                      Velvetleaf                                                                            3G  4G,3H                                                                             -- -- --  --  --  3G  8G  2G  3G  7G  9G                      Jimsonweed                                                                            3G  5G  0  0  2G  2G  5G  0   2G  2G  6G  8G  9G                      Soybean 2H  6G,5H                                                                             0  0  0   0   0   2G,2C                                                                             4G,5H                                                                             7G,5C                                                                             8G  5G,3H                                                                             9G                      Rice    5G  6G  2G 4G 5G  2G  6G  3G  7G  7G  8G  6G  8G                      Wheat   0   3G  0  0  0   0   0   5G  6G  3G  4G  2G  4G                      __________________________________________________________________________

Test C

Two ten-inch in diameter plastic pans lined with polyethylene linerswere filled with prepared Fallsington silt loam soil. One pan wasplanted with seeds of wheat (Triticum aestivum), barley (Hordeumvulgare), wild oats (Avena fatua), downy brome (Bromus tectorum),cheatgrass (Bromus secalinus), blackgrass (Alopecurus myosuroides),annual bluegrass (Poa annua), green foxtail (Setaria viridis),quackgrass (Agropyron repens), Italian ryegrass (Lolium multiflorum) andripgut brome (Bromus rigidus). The other pan was planted with seeds ofRussian thistle (Salsola kali), tansy mustard (Descuraina pinnata),Galium aparine, tumble mustard (Sisymbrium altissium) kochia (Kochiascoparia), shepherd's purse (Capsella bursapastoris), Matricariainodora, black nightshade (Solanum nigrum), yellow rocket (Barbareavulgaris), rapeseed and wild buckwheat (Polygonum convolvulus). Theabove two pans were treated pre-emergence. At the same time two pans inwhich the above plant species were growing were treated post-emergence.Plant height at the time of treatment ranged from 1-15 cm depending onplant species.

The test compounds were diluted with a nonphytotoxic solvent and sprayedover-the-top of the pans at two rates of application. An untreatedcontrol and a solvent alone control were included for comparison. Alltreatments were maintained in the greenhouse for 20 days at which timethe treatments were compared to the controls and the effects visuallyrated. The recorded data are presented in Table C. The data indicatethat the compounds tested have potential utility for the pre- and/orpost-emergence weed control of certain weed species in cereal crops suchas wheat and barley.

                                      TABLE C                                     __________________________________________________________________________             Compound 1       Compound 3                                                   Pre-Emergence                                                                         Post-Emergence                                                                         Pre-Emergence                                                                         Post-Emergence                              Rate kg/ha                                                                             0.06                                                                              0.015                                                                             0.06                                                                              0.015                                                                              0.015                                                                             0.06                                                                              0.015                                                                             0.06                                    __________________________________________________________________________    wheat    1C,2G                                                                             1C,1G                                                                             3G  0    6G  7G  2G  6G                                      barley   3G  2G  3G  0    4G  6G  4G  6G                                      wild oats                                                                              1C,5G                                                                             4G  5G  3G   5G  8G  3G  7G                                      downy brome                                                                            2C,6G                                                                             4G  8G  5G   8G  8G  0   4G                                      cheatgrass                                                                             9C,9G                                                                             2C,8G                                                                             8C,9G                                                                             1C,7G                                                                              5G  10C 4G  7G                                      blackgrass                                                                             8C,7G                                                                             3C,6G                                                                             9C,9G                                                                             6G   1C,8G                                                                             2C,9G                                                                             5G  2C,8C                                   annual bluegrass                                                                       1C,6G                                                                             1C,5G                                                                             5C,8G                                                                             7G   8G  G   5G  8G                                      green foxtail                                                                          2G  0   1C,2G                                                                             0    2G  5G  3G  3G                                      quackgrass                                                                             8G  6G  8G  5G   8G  9G  7G  8G                                      Italian ryegrass                                                                       6G  1C,5G                                                                             5G  5G   4G  8G  4G  6G                                      ripgut brome                                                                           7G  1C,5G                                                                             3C,8G                                                                             6G   7G  2C,8G                                                                             6G  8G                                      Russian thist1e                                                                        2C,2G                                                                             1C,1G                                                                             7C,7G                                                                             2C,3G                                                                              0   1C  3G  4G                                      tansy mustard                                                                          9G  10E 10C 10C  9G  2C,9G                                                                             10C 10C                                     Galium aparine                                                                         9C,8G                                                                             1C,8G                                                                             8G  6G   9G  2C,9G                                                                             5C,9G                                                                             10C                                     tumble mustard                                                                         10C 8G  9C,9G                                                                             9C,9G                                                                              9G  10C 10C 10C                                     kochia   5G  2G  2G  0    3G  6G  5G  5G                                      shepherd's purse                                                                       10C 9C,9G                                                                             9C,9G                                                                             10C  3C,9G                                                                             9C,9G                                                                             10C 10C                                     Matricaria inodora                                                                     9G  9G  10C 7C,8G                                                                              9G  3C,9G                                                                             10C 10C                                     black nightshade                                                                       8G  1G  3G  0    7G  7G  2C  4G                                      yellow rocket                                                                          9C,9G                                                                             9G  9C,9G                                                                             8G   9G  2C,9G                                                                             10C 10C                                     rapeseed 9C,9G                                                                             5C,9G                                                                             10C 10C  2C,9G                                                                             2C,9G                                                                             9C,9G                                                                             10C                                     wild buckwheat                                                                         5C,8G                                                                             1C,5G                                                                             4C,7G                                                                             2C,7G                                                                              7G  2C,8G                                                                             2C,8G                                                                             7C,9G                                   __________________________________________________________________________

Test D

Two compounds from within the scope of the invention were dissolved in anon-phytotoxic solvent and applied to rice which had been transplantedthree days previously into simulated paddies. The paddies also containedplantings of barnyardgrass, water chestnut and arrowhead, serious weedproblems in rice fields. The test was maintained in a greenhouse. Plantresponse ratings were made five to eight weeks after applicationutilizing the rating system as described for Test A. The data aresummarized in Table D. At least one of the compounds tested has utilityfor selective weed control in rice.

                  TABLE D                                                         ______________________________________                                              Rate             Barnyard-                                                                             Water   Arrow-                                 Cmpd. g/ha    Rice     grass   Chestnut                                                                              head                                   ______________________________________                                        1     10      1G       7H      3G       9G                                          20      4G,5I    9H      7G      9G,4C                                        40      7G,5I    10C     9G      10E                                          80      8G,5I    10C     10C     10E                                    2     10      0        0       0       0                                            40      0        4G      0       0                                      3     10      0        9E      0        5G                                          40      0        9E      8G      10G                                    3     10      0        8C      7G      10E                                          20      0        9C      8G      10G                                          40      3G,5I    9C       9G,3C  10E                                          80      3G,5I    9C      10G,1C  10E                                          100     4G,5I    9C      10G,4C  10G,5C                                       120     3G,5I    10C     10C     10G,6C                                 4     20      3G,5I    5G      9G      0                                            40      4G,5I    9C      9G      0                                            80      7G,5I    10C     10G,2C  2G,2H                                  5     20      6G,5I    9C      0        9G                                          40      7G,5I    9C      7G      10G                                          80      8G,3C    9G      1G      10G                                    ______________________________________                                    

Test E

The test chemicals, dissolved in a non-phytotoxic solvent, were appliedin an overall spray to the foliage and surrounding soil of selectedplant species. One day after treatment, plants were checked for rapidburn injury. Approximately fourteen days after treatment all specieswere visually compared to untreated controls and rated for response totreatment. The rating system was as described previously for Test A. Thedata are presented in Table E.

All plant species were seeded in Woodstown sandy loam soil and grown ina greenhouse. The following species were grown in soil contained inplastic pots (25 cm diameter by 13 cm deep): soybeans, cotton, alfalfa,corn, rice, wheat, sorghum, velvetleaf (Abutilon theophrasti), sesbania(Sesbania exaltata), sicklepod (Cassia obtusifolia), morningglory(Ipomoea hederacea), jimsonweed (Datura stramonium), cocklebur (Xanthiumpensylvanicum), crabgrass (Digitaria spp.), nutsedge (Cyperus rotundus),barnyardgrass (Echinochloa crusgalli), giant foxtail (Setaria faberii),and wild oats (Avena fatua). The following species were grown in soil ina paper cup (12 cm diameter by 13 cm deep): sunflower, sugar beets, andrape. All plants were sprayed approximately 14 days after planting.Additional plant species, such as johnsongrass and field bindweed, aresometimes added to this standard test in order to evaluate unusualselectivity.

Several of the compounds tested by this procedure are useful for thepost-emergence control of weeds in wheat and rice.

                                      TABLE E                                     __________________________________________________________________________    Over-the-Top Soil/Foliage Treatment                                                   Compound 1                                                                            Compound 2  Compound 5                                        Rate g/ha                                                                             125 31  62  15  4   62  15  4                                         __________________________________________________________________________    Soybeans                                                                              9G,8C                                                                             10C 4G,4C                                                                             2G,3C                                                                             1G,1C                                                                             9C  9G  9G                                        Velvetleaf                                                                            9G,9C                                                                             8G,2C                                                                             9G,6C                                                                             8G,4C                                                                             4G  8G  10C 4G                                        Sesbania                                                                              9G,4C                                                                             8G,4C                                                                             9G,5C                                                                             8G,4C                                                                             8G,4C                                                                             8G  6G  3G                                        Sicklepod                                                                             4G,3C                                                                             4G,4C                                                                             0   0   0   2G  2G  1G                                        Cotton  10C 10C,4C                                                                            9G  9G  8G  9G  8G  8G                                        Morningglory                                                                          9G,8C                                                                             7G  8G,7C                                                                             7G,2C                                                                             2C  6G,5C                                                                             0   0                                         Alfalfa 9G,5C                                                                             8G,5C                                                                             8G  6G  0   7C,4G                                                                             9G  4C,6G                                     Jimsonweed                                                                            9G  4C  0   0   0   9G  8G  8G                                        Cocklebur                                                                             9G,2C                                                                             9G,2C                                                                             --  0   0   7G  6G  6G                                        Sunflower                                                                             10C 10C 9G,5C                                                                             9G,2C                                                                             9G,2C                                                                             10C 10C 10C                                       Rape    10C 10C 9G,4C                                                                             9G  7G,4C                                                                             8G 8G                                                                             8G                                            Sugar beets                                                                           8G  5G  8G  6G  6G  10C 5G  4G                                        Corn    9G,8C                                                                             7C  8G,5H                                                                             5G,2C                                                                             0   10C 10C 8G                                        Crabgrass                                                                             0   0   0   0   0   8G  2G  2G                                        Rice    1G  0   0   0   0   2G  2G  1G                                        Nutsedge                                                                              5G  0   9G  0   0   0   0   0                                         Barnyardgrass                                                                         7G  6G  7G,3C                                                                             5G  2G  5G  4G  3G                                        Wheat   2G  0   0   0   0   4G  2G  0                                         Giant foxtail                                                                         7G  0   6G  4G  2G  3G  2G  0                                         Wild Oats                                                                             6G  2G  0   0   0   2G  1G  0                                         Sorghum 5G  5G  5G,3C                                                                             3G  0   9C  8C  8G                                        Johnsongrass                                                                          8G,8C                                                                             3G  4G  2G  0   8G  5C,6G                                                                             5G,4C                                     Field Bindweed                                                                        0   3G  4G  0   0   0   0   0                                         __________________________________________________________________________

What is claimed is:
 1. A compound selected from ##STR67## wherein W isO, S, SO or SO₂ ;W₁ is O, S, SO or SO₂ ; R₁ is H or CH₃ ; R₂ is H or C₁-C₄ alkyl; R₃, R₄, R₅, R₆ and R₇ are independently H or CH₃ ; A is##STR68## X is CH₃, OCH₃ or Cl; Y is C₂ H₅, CH₃, OCH₃, OC₂ H₅, CH₂ OCH₃,NH₂, NHCH₃, SCH₃, N(CH₃)₂, CH(OCH₃)₂ or ##STR69## and Z is CH;providedthat when X is Cl, then Y is NH₂, NHCH₃, N(CH₃)₂ or OCH₃.
 2. Compoundsof claim 1 Formula I where W and W₁ have identical values.
 3. Compoundsof claim 1 Formula II where W and W₁ have identical values.
 4. Compoundsof claim 2 where R₇ is H.
 5. Compounds of claim 3 where R₇ is H. 6.Compounds of claim 4 where R₂ is H or CH₃.
 7. Compounds of claim 6 whereY is CH₃ or OCH₃.
 8. Compounds of claim 7 where W and W₁ are O or S. 9.Compounds of claim 7 where W and W₁ are SO or SO₂.
 10. The compound ofclaim 1 which isN-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl,-1,3-benzodioxole-4-sulfonamide.11. The compound of claim 1 which isN-[(4,6-dimethylpyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide.12. The compound of claim 1 which isN-[-(4,6-dimethoxypyrimidin-2-yl)aminocarbonyl]-2,2-dimethyl-1,3-benzodioxole-4-sulfonamide.13. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 1and at least one of the following: surfactant solid or liquid diluent.14. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 2and at least one of the following: surfactant, solid or liquid diluent.15. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 3and at least one of the following: surfactant, solid of liquid diluent.16. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 4and at least one of the following: surfactant, solid of liquid diluent.17. A composition suitable for controlling the growth of undesiredvegetation which comprises an effective amount of a compound of claim 5and at least one of the following: surfactant, solid of liquid diluent.18. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 1. 19. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim
 2. 20. A method forcontrolling the growth of undesired vegetation which comprises applyingto the locus to be protected an effective amount of a compound of claim3.
 21. A method for controlling the growth of undesired vegetation whichcomprises applying to the locus to be protected an effective amount of acompound of claim
 4. 22. A method for controlling the growth ofundesired vegetation which comprises applying to the locus to beprotected an effective amount of a compound of claim 5.